The condensation product obtained by heating and fusing p-benzoxybenzenesulfonamide with 2- or 6-chloropyrimidine was assumed to be p-{pyrimidyl-(2 or 6)}-oxybenzenesulfobenzamide formed by the intramolecular rearrangement of the benzoyl radical to N and, at the same time, the freed OH radical reacting with chloropyrimidines.

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The condensation product obtained by heating and fusing p-benzoxybenzenesulfonamide with 2- or 6-chloropyrimidine in the presence of alkali carbonate was synthetically proved to be p-(pyrimidyl-(2 or 6))-oxybenzenesulfobenzamide.

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When p-acyloxybenzenesulfonamide is heated in the presence of alkali carbonate, acylradical easily undergoes intramolecular rearrangement to form p-hydroxybenzenesulfoacylamides in a good yield.

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When p-pyrimidyl- or p-pyridyl-(2)-oxybenzenesulfonamide, obtained by the condensation of p-hydroxybenzenesulfonamide with 2-chloropyrimidines or 2-chloropyridines, is heated and fused in the presence of alkali carbonate, pyrimidyl-(2) or pyridyl-(2) radical undergoes rearrangement to N and 2-(p-hydroxybenzenesulfamino)-pyrimidines or -pyridines are obtained in a good yield.

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(1) It was found that when p-{pyrimidyl-(6)}-oxy-benzenesulfonamide, obtained by the condensation of p-hydroxybenzenesulfonamide and 6-chloropyrimidine, is heated and fused in the presence of alkali carbonate, pyrimidyl-(6) radical undergoes rearrangement to N to form 6-(p-hydroxybenzenesulfamino)-pyrimidine.
(2) when p-{pyrimidyl-(2 or 6)}-oxy-benzenesulfonamides are heated and fused with 2- or 6-chloropyrimidines in the presence of alkali carbonate, O, N-dipyrimidyl compounds are formed. In this condensation, two kinds of reactions were found to take place. In one reaction, the pyrimidyl radical in the para position does not undergo rearrangement to N but chloropyrimidine condenses with sulfonamide radical to form a dipyrimidyl compound. In the other, the initial pyrimidyl radical attached to the ortho position undergoes intramolecular rearrangement to N and a secondary pyrimidyl radical reacts with the newly formed OH radical to yeild a dipyrimidyl compound.

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As an isoquinoline derivatives resembling papaverine in its structure, 1-(3′-methoxy-4′-hydroxyphenyl)-3-methyl-6, 7-methylenedioxyisoquinoline was synthesized and led to water-soluble sodium salt in order to examine its physiological activity. Vanillin benzyl ether was oxidized to 3-methoxy-4-benzyloxybenzoic acid, with which α-methyl-β-methoxy-β-(3, 4-methylenedioxyphenyl)-ethylamine was condensed by the Shotten-Baumann reaction. This acid amide was cyclized to the phenolic base, m.p. 217°, after debenzylation.

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Hydrazides of 4-nitro- or 3, 4-methylenedioxyhippuric acid were respectively condensed with α-methyl-β-(3, 4-methylenedioxyphenyl)-ethylamine into acid amides and by cyclization with POCl₃, two kinds of imidazoisoquinoline derivatives with 2 molecules dehydrated were obtained as 9, 10-methylenedioxy-3-(4′-nitrophenyl)-5-methyl-5, 6-dihydrobenzoglyoxalocoline and 9, 10-methylenedioxy-3-(3′, 4′-methylenedioxyphenyl)-5-methyl-5, 6-dihydrobenzoglyoxalocoline. The latter acid amide was also obtained in a good yield by the fusion of the above-mentioned amine and ethyl 3, 4-methylenedioxyhippurate.
An acid amide was obtained by the condensation of α-methyl-β-(3, 4-methylenedioxyphenyl)-β-methoxyethylamine and 3, 4-dimethoxyhippuric acid azide, and cyclized, but it is unknown whether two molecules were dehydrated.

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Three kinds of aminoisoquinoline derivatives having amino radical in 1-, 3- or 4-position of N-containing ring were synthesized in order to examine their chemical properties and physiological activities. Ethyl 1-phenyl-6, 7-dimethoxyisoquinoline-3-carboxylate was prepared and led to benzyl 1-phenyl-6, 7-dimethoxyisoquinolyl-3-carbamate by the usual method through its hydrazide and azide. Finally, 1-phenyl-3-amino-6, 7-dimeth-oxyisoquinoline was obtained by the Sugasawa's improved method of the Curtius degradat on. The saponification of benzylurethane was made by treatment with a mixture of 20% HCl and glacial AcOH (1:1) or by a catalytic reduction with Pd in a good yield.

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In order to synthesize isoquinoline derivative having amino radical in 4-position, 1-phenyl-4-benzoylamino-3, 4-dihydro-6, 7-dimethoxyisoquinoline was synthesized. Benzylurethane was obtained from 3, 4-dimethoxyphenylsuccinic acid by way of its ester, hydrazide and azide by the usual method and converted into diamine by the Sugasawa's improved Curtius' degradation. It was led to dibenzoyl-3, 4-dimethoxyphenyl-ethylenediamine, by the Schotten-Baumann reaction, and cyclized to the above-mentioned compound by POCl₃. In this case, it was difficult to cyclize by using P₂O₅, and toluene gave a better yield than benzene as a solvent. Analytical results indicated that imidazolidone-type urethane had been formed as a by-product, besides dibenzylurethane. The saponification of benzyl derivatives will be reported later.

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The antibacterial action of sulfanilamide derivatives, substituted by aliphatic radical in N¹-position, is nearly the same as that of sulfanilamide, but the antibacterial action of the derivatives substituted by aromatic radical in N¹-position increased generally, especially the action of Irgafen was remarkable. The action of the derivatives substituted by heterocyclic radical in N¹-position increased remarkably, especially in case of sulfathiazole and sulfadiazine. The antibacterial action of sulfanilamide derivatives, substituted by aliphatic or aromatic radical in N⁴-position, was recognized to be weaker or disappeared. The antibacterial action was not recognized in the derivatives of aromatic sulfonamide substituted in para-position or nitrogen-containing heterocyclic sulfonamides. The actions of 4, 4′-diamino-diphenyl sulfone, and 4-aminophenyl 5′-amino-2′-pyridyl sulfone were the same as that of sulfapyridine but the action of derivatives substituted by aliphatic or aromatic radical was found to be remarkably weaker or disappeared.

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The intensity of the inhibitory action against bacterial growth of sulfa drugs is nearly parallel to their antagonistic activity against antagonists, i.e. p-aminobenzoic acid, bouillon, meat extract and peptone. In other words, compounds which are not easily affected by the hindrance of antagonists have been recognized to possess stronger inhibitory action against bacterial growths.

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Comparing the three series of the experimental results, i.e. antibacterial activity of sulfa drugs, behavior of sulfa drugs against their antagonists using certain bacteria as test organisms and the adsorption affinity of sulfa drugs to charcoal, the strengthening of adsorption affinity by combining aromatic or heterocyclic radicals with sulfa drugs was assumed to be an important factor in intensifying the antibacterial action.

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The curve which shows the relationship between acidity and antibacterial activity of N¹-substituted derivative of sulfanilamides has been found to have one maximum. The reason is thought to be due to the fact that, though SO₂-radical in ionic type is more negative, the negativity of ionic or molecular type decreases as the acid dissociation constant decreases. Therefore, the relationship between acid dissociation and antibacterial activities of sulfa drugs is thought to be directly relative to the negativity of SO₂-radical. The theory of Bell and Roblin is thought to be applicable under the condition of pH 7.0. In spite of the general weakness or disappearance of antibacterial action in N⁴-substituted compounds of sulfa drugs, the fact that the acid dissociation constant is almost the same as that of the original, shows that the relationship between chemical structure and antibacterial activities cannot be explained only by acid dissociation. The theories which explain the relationship between chemical structure and antibacterial activities of sulfa drugs by ionic-type or resonance-type theory present some doubts.

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The intensity of the inhibition of bacterial growth by sulfanilamide and diaminodiphenyl sulfone derivatives were found to be nearly paralell to the antagonistic power against antagonists such as p-aminobenzoic acid, bouillon, meat extract and peptone. In other words, the compounds which were difficult to be affected by the antagonists were found to be the strongest in inhibiting bacterial growth. This was thought to be that the antagonistic activities would become stronger as the affinity to bacteria became stronger.

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The results of antiseptic test against soy sauce were found to be almost ineffective at a concentration of 0.001-0.01% in 8 compounds of cinnamic acid series; i.e. o-hydroxy-, 3, 4-dihydroxy-, 3-methoxy-4-hydroxy-, β-methyl-2, 4-dihydroxy-, β-methyl-2, 5-dihydroxy-, p-dimethylamino-cinnamic acids, ethyl p-dimethylamino-cinnamate and cinnamic acid.

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1) The natural or fatigue states immediately preceding death of albino-rats, killed by electric shock or by hard blow, did not have any conclusive effect on the change in the amount of volatile basic nitrogen and amino-nitrogen in the muscle after death. Body deteriorated more rapidly in rats killed by blow than by electric shock.
2) In rats killed by electric shock, the number of bacteria was always more abundant in the fatigued group than in the normal group. However, comparative results of the degree of putrefaction by macroscopic observation was not always in accordance with the results of bacterial numbers but coincided with the amount of volatile basic nitrogen.
3) The value of pH transferred rapidly to acid region after death, and after 12-18hrs. (at 37°), it began to move toward alkaline region. In this case, pH value moved more in the alkaline side of fatigued group than the normal group.
4) Killing by electric shock transfers the muscle pH to acid region. In this case, muscle pH of normal rat showed more acidity than that of fatigued group. The cause of this phenomenon is due to the rapid increase of lactic acid by the sudden and strong excitation of the muscle by electric shock.
5) Rigor mortis in those killed by electric shock was stronger and stayed longer than in those killed by blow.

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Using cymene and carvacrol as starting materials, two bz-alkyl-isoquinoline derivatives, 1-phenyl-5-methyl-8-isopropyl-3, 4-dihydroisoquinoline and 1-phenyl-5-isopropyl-7-methoxy-8-methyl-3, 4-dihydroisoquinoline, were synthesized.

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A new method for the synthesis of β-dimethylaminoethyl-benzhydryl ether (benadryl base) was developed. By warming benzhydrol and ethylene chlorohydrin in the presence of small amount of conc. H₂SO₄, β-chloroethyl-benzhydryl ether was produced in a good yield, which was followed by heating with alcoholic dimethylamine solution in a sealed tube, giving benadryl base. This method is also suitable for a large scale production.

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By applying the synthetic method described in the foregoing paper, the following basic benzhydryl ethers were prepared: γ-Dimethylaminopropyl benzhydryl ether, colorless liquid, b.p₄ 174-176°; methiodide, colorless plates, m.p. 180-181°; picrate, yellow prisms, m.p. 117-119°. β-Dimethylaminoethyl p-dimethylaminobenzhydryl ether, pale yellow liquid, b.p₁ 175-182°; methiodode, colorless prisms, m.p. 175-177°; picrate, yellow plates, m.p. 117-119.5°; hydrochloride with 1/2 H₂O, small scales, m.p. 138.5-139.5°. β-Dimethylaminoethyl bis-(p-dimethylamino)-benzhydryl ether, white needles, m.p. 97-97.5°.

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When an aqueous solution of thiamine hydrochloride was heated, the following were formed: 2-methyl-4-amino-5-aminomethyl-pyrimidine, 2-methyl-4-amino-5-hydroxymethyl-pyrimidine, 4-methyl-5-β-hydroxyethyl-thiazole, γ-aceto-γ-mercaptopropyl alcohol, thiochrome and formic acid. Therefore, it was assumed that thiamine hydrochloride existed in the aqueous solution in the state of equilibrium of ammonium-, carbinol- and thiol-types. The equilibrium, however, is likely to be more inclined towards the stable ammonium-type.

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1) The synthesis of 1, 9-dimethyl-3, 7-dihydroxydibenzofuran from orcinol dimethyl ether was reëxamined and, in connection with the observations recognized during the synthesis, chlorination of orcinol, orcinol dimethyl ether, methyl p-orsellate and 2, 2′-dimethyl-4, 6, 4′, 6′-tetramethoxybiphenyl was examined.
2) The antibacterial action of orcinol and its related compounds, including chlorinated compounds obtained by these reactions, was tested (cf. Table II.).

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Several halogenated derivatives of 4-hydroxybiphenyl ether were synthesized from 4-hydroxybiphenyl ether. 3-Chloro-4-hydroxybiphenyl ether (II) was obtained by the action of sulfuryl chloride at 85°. 3-Bromo compound (I) and 3, 5-dibromo (III) were obtained by bromination with bromine in carbon disulfide solution at room temperature. By the condensation of 2mol. potassium salt of 3-bromo-4-hydroxybiphenyl ether (I) at 155-165°, using copper powder as the catalyst, 2, 6-diphenoxy diphenylene dioxide (IV), m.p. 161-162°, was obtained. By the chlorination of 4-hydroxybiphenyl ether with chlorine in glacial acetic acid solution, yellow needles, m.p. 273-275° (decomp.), were obtained and this was assumed to be octachloro-4-hydroxybiphenyl ether. Growth inhibitory actions of these compounds against Staphylococcus aureus, B. coli and Mycobacterium tuberculosis are shown in the accompanying table.

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Domesticine methyl ether, which had been known to exist only in the fruit of Nandina domestica, has been found from the trunk bark and the roots. Nandinine, whose existence had been questionable, was not found by the authors. Moreover, it was found that domesticine does not show a constant melting point of 116-117° but gives different melting points under various recrystallization, solvents and other conditions. These melting points were: m.p. 115-116° when recrystallized from water and methanol, m.p. 84-85° when recrystallized from absolute methanol or benzene, and m.p. 152-153° (decomp.) when dried at 60° over phosphorus pentoxide in vacuum. By the reduction of the quarternary base, tetrahydroberberine and tetrahydrojatrorrhizine were proved. In other words, roots and trunk bark of Nandina domestica was found to contain jatrorrhizine, as well as the hitherto-known berberine, as the quarternary base. It was also found that Nandina domestica did not contain biscoclaurine type base.

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The ergot alkaloids known up to the present number 12 of six pairs, classified into three groups of ergotoxine, ergotamine and ergometrine. The decomposition products of these alkaloids by acids or alkalis are amino acids or substances which can be directly derived from amino acids and it gives rise to assumption that a close relationship exists between alkaloids and amino acids. The authors, therefore, carried out detection of free amino acids by means of paper chromatography from cultivated ergots on rye and wheat, from natural ergots on Elymus mollis T., Imperata cylindra Koenigii and Sasa nipponica and from ergots stored for a long period of time, in order to clarify the said relationship. Aqueous digested solution of ergots containing amino acid, contained so large an amount of potassium salts that it cannot be used as a sample for chromatography. For example, aqueous digested solution of ergots of rye gives continuous chromatographic spots and the development is not so sufficient that individual amino acids cannot be detected. In order to examine the effect of occluded salts on paper chromatography, sodium chloride and acetate were added to the known amino acid solution in various concentrations, chromatographed with phenol and n-butanol as developers, and changes in Rf values of each spot were observed.

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Detection of free amino acids in cultivated and natural ergots was carried out by means of paper chromatography. Amino acids were purified as mercury salts. At the same time, total alkaloids and substances coloring by ninhydrin in ergots were also examined. Aspartic acid, glutamic acid, alanine, histidine, valine, phenylalanine, leucine and an unknown spot just above the left shoulder of alanine, were detected in the paper chromatograms of ergots of Secale cereale, Imperata cylindra var. Koenigii and Sasa nipponica. Specific spots detected were tyrosine in ergots of Secalecereale and Sasa nipponica, and glycine in those of Secale cereale and Triticum vulgare. Histamine was found in many of the ergots. Only aspartic and glutamic acids, alanine and phenylalanine were detected in ergots stored for 27 years. Amino acids in rye corn were examined for control but these were negative. The total alkaloids were found to be about 0.5% in rye ergots, and over 1% in ergots of Elymus mollis (Claviceps litoralis).

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Conditions for the reduction of alkylylresorcinols by zinc amalgam and hydrochloric acid were examined.

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As a result of tests for the antiseptic action of ethyl thiocyanoacetate against soy sauce, it was found to be far stronger than salicylic acid, benzoic acid, butyl p-hydroxybenzoate, α-naphthol, β-naphthol or allyl-mustard oil.

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Antiseptic actions against soy sauce were compared of the esters of acetic, chloroacetic and thiocyanoacetic acids and it was found that methyl, ethyl, isopropyl, isobutyl and isoamyl esters of chloroacetic acid possessed stronger action than those of acetic acid, and those of thiocyanoacetic acid were the strongest.

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Antiseptic actions against soy sauce were compared of the ethyl esters of propionic, butyric, isovaleric, caproic, capric and lauric acids and their α-bromo and α-thiocyano derivatives. It was also found in these cases that the esters of thiocyanofatty acids possessed the strongest action followed by the esters of bromofatty acids and the original fatty acids.

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6-Nitropiperonylic acid was prepared from 6-nitro-piperonal according to Mameli's method and converted by PCl₅ into the chloride, which was condensed with diethyl malonate in benzene solution at 30-40° by the Bischoff's method to diethyl 3, 4-methylenedioxy-6-nitrobenzoyl molonate (I), oily liquid. By the reduction of the crude (I) with Sn and conc. HCl in hot alcoholic solution, 2, 4-dihydroxy-6-methylenedioxyquinoline was formed as white crystals, m.p. over 320° (nitroso compound: dark reddish purple crystals, m.p. 241-242° (decomp.)). 2, 4-Dihydroxy-6, 7-methylenedioxyquionoline-3-aldehyde (III) was obtained by adding the excess of CHCl₃ slowly to (II) in 15% NaOH on a water bath. Yield, 53.7% of the theory. Almost colorless leaflets (from alcohol), m.p. 316-318° (decomp.). Phenylhydrozone of (III): yellow needles, m.p. 226°.

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The manner of decomposition as a result of supersonic wave radiation was examined using polystyrene of 1, 200 degree of polymerization, with benzene or toluene as solvent. Observations were made on the change in the decomposition rate by the change of intensity, and the difference by the use of different solvents. At an intensity of 1g. wt./t (7.5mm.)² and radiation pressure of 554erg./cm³, supersonic wave radiation of 10 minutes reduced the polymerization degree to 620, to 470 in 30 minutes, and 345 in 60 minutes. When the intensity was varied but radiated for 5 minutes, the polymerization degree was reduced to 1, 000 by an intensity of 0.2g. wt., to 700 by 1g. wt., and 630 by 1.4g. wt., showing a somewhat large difference by the change in intensities. There were no perceptible difference by the change of solvents as long as the intensity of the radiation in the solution remained constant. It was found that, if the wave source was of the same intensity, supersonic waves show larger energy density in toluene than in benzene.

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N-Methyl-α-quinolone type base was synthesized by the oxidation of ar.-methiodide of quinine by alkaline potassium ferricyanide. Few unknown derivatives of quina base of the same type were also synthesized. 1′-Methyl-2′-phenyl-(1′, 2′)-dihydro-dihydroquinine was synthesized from ar.-methiodide of hydroquinine by the utilization of Grignard reaction, and its reduction by tin and hydrochloric acid yielded py.-tetrahydro compound.

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A total of 14 kinds of 2-phenoxy, 2-allyloxy, 2-guanidino and 2-anilido compounds were synthesized from 2-chloro-6-nitrobenzothiazole. By reacting dimethyl sulfate on 2-amino-6-R-benzothiazoles (where R=Cl, NO₂, OCH₃ and OC₂H₅), the corresponding 2-amino-3-methyl-6-R-2, 3-dihydrobenzothiazoles were prepared.

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Twelve kinds of aminovinyl compounds were synthesized using quinalidine methiodide, 6-methoxyquinaldine methiodide, 6-ethoxyquinaldine methiodide and 6-methoxybenzothiazole methiodide. Nine kinds of trimethine cyanines were synthesized from 2-methylbenzothiazole methiodide, 2-methyl-6-bromobenzothiazole ethiodide, 6-dimethylaminoquinaldine methiodide, 5 (x)-dimethylaminoquinaldine methiodide, 7 (x)-dimethylaminolepidine ethiodide, 9-methylacridine methiodide (ethiodide) and 2-methyl-(β)-naphthoquinoline ethiodide.

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Addition of 4cc. of fuming HCl to a mixture of 0.5cc. of 0.05-0.1% aqueous solution of sugar and 0.1cc. of 1% alcoholic solution of isoevodiamine, and placing the mixture at about 37°, result in the development of a reddish purple color within 5 minutes which changes to an intensive violet color if ketohexose is present. There is no such color reaction in the presence of aldohexose, methylpentose and pentose. Detection of ketohexose by this method is successful even in a concentration of 0.0001% (0.5γ in 0.5cc.) in 60 minutes. Isoevodiamine used in these tests was a product derived from evodiamine, an alkaloid of Evodia rutaecarpa Hook. fil. et Thoms.

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Flavonol derivatives, such as rutin, show a sensitive yellow coloration by aluminum ion. For example, absorption spectrum of the aluminum compound of rutin shows absorption maxima at 274mμ and 416mμ. The authors carried out determination of flavonols by the colorimetry of their yellow coloration in 0.75% aluminum acetate solution (pH 3.74). The yellow coloration of the flavonol derivatives produced by aluminum or magnesium ion is very similar to that of potassium chromate solution so that it would be convenient to prepare a series of standard solutions of the chromate prior to colorimetry. Partition paper chromatography of flavonols, such as rutin, myrcitrin, quercitrin, quercetin, myrcetin and morin, was carried out and, after development with BuOH:H₂O:AcOH=5:4:1, or PhOH:H₂O:AcOH=40:9:1 as solvents, flavonol spots were sprayed with 2.5% aluminum acetate, dried, and their Rf values measured.
Further, crude methanolic extracts of about ten kinds of plants containing flavonol, such as rutin and kaempherol, were also studied by the above method.

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Paper partition chromatography was carried out using BuOH:H₂O:AcOH=5:4:1, or PhOH:H₂O:AcOH=40:9:1, as developing solvents, on over 50 kinds of basic compounds (I). Dragendorf's reagent (II), diluted to 5 volumes, was sprayed on the dried filter paper, and the spot of (I) was observed. Since some of the primary, secondary and tertiary bases do not precipitate with (II), 5% methanolic KOH and 10% methanolic solution of dimethyl sulfate are sprayed consecutively, and warmed at 70° for 5 minutes to complete N-methylation. This is sprayed with 10% acetic acid to neutralize the excess of the alkali, and (II) sprayed, by which all of (I) can be identified. The orange colored portion by (II) is a precipitate and is not washed out by water. The colored portion is cut out, extracted with a small amount of hot water, (II) added, and cooled slowly, by which orange precipitate having characteristic crystalline form can be detected under the microscope. This, therefore, is another method of identifying (I), besides its Rf value. This method is thought to have an extensive application. The authors examined methanolic extracts containing corresponding mineral acid of over 10 kinds of crude drugs containing (I) by this method and proved the presence of (I) in each.

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0.05-0.1mg. of organic dibasic acids was placed in a small test tube with 1-2mg. of polyphenols, such as resorcinol, cathecol, hydroquinone, phloroglucinol and pyrogallol, one drop of conc. sulfuric acid added and heated in an oil bath of 130° for 5 minutes. The reaction product was dissolved in a small amount of alkali and submitted to paper partition chromatography (solvent, BuOH:H₂O:AcOH=5:4:1, allowed to stand quietly for 4-5 days after shaking). In the case of resorcinol, phloroglucinol and pyrogallol, strong fluorescent substance of fluorescein- or umbelliferon-type is assumed to be produced and Rf value and spot of fluorescence specific to each organic acid were shown by radiation of ultraviolet rays. Among over 20 substances tested, the strongest spot of fluorescence was shown when 1, 2-dicarboxylic acid, such as citric, maleic, phthalic, succinic and tartaric acids, was reacted with resorcinol. When the reaction products which are known for their color reaction are put to paper chromatography, more accurate identification can be carried out.

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Various structures have been proposed for penicillin and, in spite of the successful synthesis of penicillin by du Vigneaud, et al., it has not yet reached a decisive stage. As a model of penicillin synthesis, the authors reacted 2-phenyl-4-ethoxymethylene-5-oxazolone with glycine (and its ester), added benzylthiol to the reaction product in the presence of sodium alcoholate, and discussed the structure of the final product. This compound was proved to be benzyl α-benzoylamino-β-carboxy (or carbethoxy)-methyl-aminothioacrylate, and the authors pointed out that this compound corresponds to the model of the unsaturated thiolactone formula of penicillin proposed by Cavallito.

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As a result of antiseptic tests of sodium octyl sulfate, sodium dodecyl sulfate, sodium tetradecyl sulfate and sodium cetyl sulfate against soy sauce, sodium dodecyl sulfate and sodium tetradecyl sulfate were found to have a very strong antiseptic action, inhibiting the growth of mold for 60 days at a concentration of 0.001%. On the contrary, mold began to grow at a concentration of 0.01% of sodium octyl sulfate on the 45. th day, and at a concentration of 0.01% of sodium cetyl sulfate on the 16th day. These facts showed that there were much difference between the former and the latter compounds in their antiseptic activity against soy sauce.

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Following seven compounds were tested as to their antiseptic actions against soy sauce: m-Nitrocinnamic acid, ethyl p-nitrocinnamate, m-aminocinnamic acid hydrochloride, p-hydroxycinnamic acid, phthalidene-acetic acid, phthalimidene-acetic acid, and methylene-phthalimidine. These were found to have almost no antiseptic acitivities at the concentration of 0.001-0.01%.

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Phenoxthin-3, 6-disulfochloride, m.p. 149°, was obtained by the sulfonation of phenoxthin with conc. sulfuric acid, followed by reacting phosphorus pentachloride to its sodium salt. By reducing this compound with tin and hydrochloric acid, the corresponding 3, 6-mercapto compound was obtained, but this compound was very unstable and had a tendency to transfer easily to the disulfide type. Its dimethyl ether, m.p. 68-69°, and diacetate, m.p. 108-109°, were both obtained as stable compounds.

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Diquinoline-6, 8′-oxide was synthesized by the Ullman condensation of 6-bromoquinoline and 8-hydroxyquinoline, and diquinoline-8, 8′-oxide, by the same condensation of 8-bromo and 8-hydroxyquinolines. Tetrahydro and N-methyl-tetrahydro derivatives of these compounds were also prepared.

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γ-Aceto-γ-acetoxypropyl (2-methyl-4-aminopyrimidyl-5)-methyl-dithiocarbamate (III) was obtained in a good yield by the condensation of 2-methyl-4-amino-5-aminomethyl-pyrimidine (I), γ-aceto-γ-chloropropyl acetate (II) and CS₂ in the presence of NH₃. (III) gives 3-(2′-methyl-4′-aminopyrimidyl-5′)-methyl-4-methyl-5-β-hydroxyethylthiothiazolone (2) (IV) by the action of hydrochloric acid, and 2-thio-7-methyl-1, 2, 3, 4-tetrahydropyrimido-(4, 5-d)-pyrimidine (V) by the action of caustic alkali or by heating at 170°. (III) is also obtained by heating amonium (2-methyl-4-aminpoyrimidyl-5)-methyldithiocarbamate (VI) and (II) in alcohol, with a byproduct of the hydrochloride of (III) and NH₄Cl. The hydrochloride of (III) can also be obtained by adding the calculated amount of hydrochloric acid to (III) or by heating (III) with (II) and NH₄Cl in methanol, and it reverts back to (III) by the action of NaHCO₃. By heating the hydrochloride of (III) at 180°, the acetate of (VI) is produced. The reaction, in which (III) is obtained by the condensation of (I), (II) and. CS₂ in the presence of NH₃, is not assumed to produce (VI) as an intermediate, so that the above two reactions must have a different reaction mechanism.

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Capillary analysis was utilized for the determination of bitter crude drugs by which the time required was shortened to within four hours whereby capillary images can be prepared and compared. It was found that Radix Gentianae Scabrae, Radix Gentianae, Herba Swertiae, Folium Trifolii fibrini, Herba Amethystanthi and Lignum Picrasmae can be fully distinguished by the tone and width of the colored zone formed in the resin and lower zones. However, those of Rhizoma Coptidis, Cortex Phellodendri and Radix Colombo belong to a similar type that aqueous, as well as alcoholic, digest solution must also be made and images from both digests compared as to the height of the image and tone of the alkaloid color zone by which individual detection would be possible.

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