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Antibacterial Activity of Drugs. II
Kanzo Okazaki, Hiroshi Kato, Takeo Wakatabe
1951 Volume 71 Issue 1 Pages
1-5
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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Antibacterial action against Staphylococci was tested with water and acetone digest extracts of 130 kinds of crude drugs, listed in Japanese Pharmacopoeia, known in Chinese medicine or as shown remedies. Results are shown in the table.
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Antibacterial Activity of Drugs. III
Kanzo Okazaki, Hiroshi Kato, Takeo Wakatabe
1951 Volume 71 Issue 1 Pages
5-9
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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Antibacterial action against Staphylococci was tested with water and acetone digest extracts of 127 kinds of crude drugs. Results are shown in the table.
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Synthesis of 2, 2′-Diamino-4, 4′-dimethyl-5, 5′-dithiazolyl Sulfone
Masaki Ohta, Kikumasa Satoh
1951 Volume 71 Issue 1 Pages
9-11
Published: January 25, 1951
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Bromination of acetonyl sulfide in benzene yields a dibromide which, by condensation with thiourea, gave bis-2-amino-4-methyl-5-thiazolyl sulfide. This sulfide can also be obtained by the reaction of 2-amino-4-methyl-5-bromothiazole and Na
2S. Acetylation of the sulfide and subsequent oxidation by 30% H
2O
2 in glacial acetic acid gave bis-2-acetamino-4-methyl-5-thiazolyl sulfone, which was hydrolyzed by conc. HCl to the objective bis-2-amino-4-methyl-5-thiazolyl sulfone.
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Yasushi Mashiko, Noriko Hayashi, Kyoko Yamamoto
1951 Volume 71 Issue 1 Pages
11-14
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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Electrolytic pressure of 4-nitro-4, 4′-dinitro- and 4-amino-4′-nitro-diphenyl ethers were determined by the polarographic method, using mercury drop electrode. The standard pressure was found to be -0.80
7 volt for 4-nitro compound (pH 7.0); -0.59
2 and -0.65
6 volt for 4, 4′-dinitro compound (pH 7.0); and -0.84
9 volt for 4-amino-4′-nitro compound (pH 7.0).
Partial reduction of 4, 4′-dinitro compound was successfully carried out by the use of (NH
4)
2S, which gave 4-amino-4′-nitro compound.
Sedative and analgesic action of 4-amino-4′-nitro- and 4-amino-biphenyl ethers was tested by its subcutaneous injection in mice.
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The Action of Cyanogen Bromide on Vitamin B1 and Thiothiazolone-(2) Compounds
Taizo Matsukawa, Takeo Iwatsu
1951 Volume 71 Issue 1 Pages
14-17
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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Examination was made on the action of CNBr on aqueous solution of vitamin B
1 hydrochloride (I) and of 3-(2′-methyl-4′-amino-pyrimidyl-5′)-methyl-4-methyl-5-β-hydroxyethyl-thiothiazolone (2) (II). It was found that (I) did not react in acid solution, either in hot or cold state, but did react in an alkaline solution, forming thiochrome (III). In this case, vitamin B
1 takes a Ψ-base form and is oxidized by CNBr. (II) reacts in both acid and alkaline solutions, forming (III). In this case, CNBr acts as a desulfurizing agent, and a thiazolone compound is assumed to be formed as an intermediate. This was proved by the formation of 3-(2′-methyl-4′-hydroxypyrimidyl-5′)-methyl-4-methyl-5-β-hydroxyethyl-thiazolone (2), m.p. 238°, by the action of CNBr from 3-(2′-methyl-4-hydroxypyrimidyl-5′)-methyl-5-β-hydroxyethyl-thiothiazolone (2), which does not form (III).
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Eukujiro Fujikawa, Shigeru Hatanaka
1951 Volume 71 Issue 1 Pages
17-18
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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Antiseptic action of following 8 compounds were tested by their power to prevent molding of soy sauce but all were found to be ineffective in the range of 0.001-0.01% concentration. Salicylic acid series compounds: Salicylic, thiosalicylic,
m-aminosalicylic,
p-aminosalicylic and
m-chlorosalicylic acids; Aminobenzoic acid series:
p-aminobenzoic acid, ethyl
p-aminobenzoate and
o-aminobenzoic acid.
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Fukujiro Fujikawa, Akimasa Tokuoka
1951 Volume 71 Issue 1 Pages
18-19
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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Antiseptic action were examined of resorcylaldehyde, orcylaldehyde, dichloro-orcylaldehyde, atranol, monochloratranol, monochloro-isoatranol, monochloro-isohaematommic acid, β-orcylaldehyde and monochloro-β-orcylaldehyde. Only atranol and monochloro-isoatranol showed stronger antiseptic action than
n-propyl
p-hydroxybenzoate used as a control by preventing the growth of mold in soy sauce during the 30-day test period in 0.003-0.005% concentration. Monochloro-β-orcylaldehyde and β-orcylaldeyde showed about the same antiseptic action as the control compound, but others were found to have only a comparatively weak action.
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Catalytic Action of Amines in Preparations of Polyethyleneglycols. (1). Catalytic Actions of Amines in Glycol-Ethylene Oxide and Diethyleneglycol-Ethylene Oxide Systems. (1)
Sadatake Kato
1951 Volume 71 Issue 1 Pages
20-24
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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Following the previous report on the industrial manufacture of polyethyleneglycol by Wurtz' reaction and by the diethyleneglycol-ethylene oxide reaction, attempt was made to remove the weak point in these methods, i.e. the necessity of high temperature, high pressure and a long period of time. It was found that the reaction could be promoted by the use of amines as a catalyst. The amines tested included aniline, dimethylaniline, pyridine, triethylamine and ammonia, all of which succeeded in promoting the reaction by the lowering of reaction temperature and pressure, and shortening the reaction period. Moreover, the presence of the catalyst did not have any effect on the system of products, giving a good yield. The amines were found to have different catalytic action, triethylamine and ammonia being the strongest, followed by pyridine and dimethylaniline, with aniline being the weakest. With one kind and a definite amount of the catalyst, the reaction speed was in proportion to the temperature. The component of the product remained constant, being independent of the temperature. In short, amines possess excellent catalytic action in the manufacture of polyethylene-glycol.
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Catalytic Action of Amines in Preparations of Polyethyleneglycols. (2). Catalytic Actions of Amines in Glycol-Ethylene Oxide and Diethyleneglycol-Ethylene Oxide Systems. (2)
Sadatake Kato
1951 Volume 71 Issue 1 Pages
24-27
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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As a result of experiments described in the previous report, it can be now summarized that the use of amines as a catalyst in the manufacture of polyethylene-glycol promotes the reaction, the degree of promotion being proportional to the amount of amines used. The reaction speed was found to be proportional to the temperature increase while the component of the product remained constant, irrespective of the use of catalysts, and the yield was generally better. The mechanism of the catalytic action of amines was assumed to be due to the dissociation of amines in glycol by which the dissociated ammonium ion transmits H
+ to generally promote the reaction. It was assumed, from their dissociation constants in water, the catalytic ability of amines coincides with the order of their basicity. Although all the amines tested were found to be a good industrial catalysts, it was concluded that ammonia, pyridine and dimethylaniline would be advantageous as industrial catalysts because of the ease of their separation from the final product.
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Catalytic Actions of Amines in Preparations of Polyethyleneglycols. (3). Catalytic Actions of Amines in Glycol-H2O-Ethylene Oxide and H2O-Ethylene Oxide Systems
Sadatake Kato
1951 Volume 71 Issue 1 Pages
27-30
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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The effect of water in the reaction of glycol-ethylene oxide system was examined and it was found that the increase in the amount of water added resulted in the increase of amount of glycol formed.
Addition of amines to the glycol-water-ethylene oxide or water-ethylene oxide system resulted in a remarkable catalytic action, the component of the products showing an increase in the amount of di-, tri- and tetraethylene-glycois formed, compared to the non-addition of amines. This phenomenon was considered from the point of reaction mechanism. In this case, alkalines possess the same trend of catalytic action but do not give as good an yield as the amines. The strength of catalytic action is approximately proportional to the alkalinity. Amines, therefore, are more advantageous as industrial catalyst in the manufacture of polyethyleneglycol since they do not corrode the installations.
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Synthesis of Aryl Orthoformates
Takaji Koyama, Takashi Asou
1951 Volume 71 Issue 1 Pages
31-32
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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Reimer-Tiemann reaction of 2, 6-dibromo-4-isoamylphenol and
p-benzylphenol were carried out and, as neutral substances, corresponding orthoformates were obtained. A phenolic substance, 2-hydroxy-5-benzyl-benzaldehyde was obtained from
p-benzylphenol.
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Reductive Acylamination in Mixtures of Benzonitrile and Benzaldehyde
Minoru Sekiya, Tomio Fujita
1951 Volume 71 Issue 1 Pages
33-35
Published: January 25, 1951
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1) Reduction, at high temperature and high pressure, of benzonitrile in the presence of benzaldehyde results in an increased yield of dibenzylamine because the aldehyde takes part in the latter's formation.
2) The action of formamide or ethyl formate was examined by the reductive formyl-amination of a mixture of benzaldehyde and benzonitrile. In the case of formamide, formylbenzylamine can be obtained in 89% yield, in a mixture of benzonitrile and benzaldehyde in a molar ratio. The use of benzaldoxime and ammonia, instead of benzonitrile, was also experimented.
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Chloromethylation of Benzoic Acid Derivatives. (3)
Taizo Matsukawa, Kenzo Sirakawa, Hajime Kawasaki
1951 Volume 71 Issue 1 Pages
36-38
Published: January 25, 1951
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Chloromethylation of 4-methylbenzoic acid was carried out in conc. H
2SO
4 by the application of paraformaldehyde and HCl-gas and 3-chloromethyl-4-methylbenzoic acid, m.p. 171.5-173°, was obtained. According to the condition of the reaction, 3, 5-dichloromethyl compound is formed at the same time.
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Masaiti Yanagita
1951 Volume 71 Issue 1 Pages
38-39
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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According to Allen and Spangler (Org. Syntheses; loc. cit.), mucobromic acid is obtained in 67-73% yield by the bromine oxidation of furoic acid. This can also be accomplished in 62-66% yield by the similar oxidation of commercial furfuraldehyde.
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Synthesis of 2-Amino-pyrimidine
Masaiti Yanagita, Seigo Fukushima
1951 Volume 71 Issue 1 Pages
39-40
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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The synthesis of 2-amino-5-chloro-pyrimidine by the condensation of malondialdehyde and guanidine was carried out with the use of chlorosulfonic acid as the condensation agent. This seems to give a better yield compared to the known method, as well as having the advantage of the reaction proceeding at a room temperature, without the application of heat.
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Torizo Takahashi, Juichiro Shibasaki, Jutaro Okada
1951 Volume 71 Issue 1 Pages
41-44
Published: January 25, 1951
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The known method of synthesizing 4-hydroxybenzothiazole from formyl-
o-anisidine was reexamined, with careful observation on the reaction conditions and the yield of products at every stage. 1-Chloro-isobenzo-1, 2, 3-dithiazoles were prepared by the application of sulfur chloride on
o-(or
p-) anisidine. These were led to
o-aminophenols and then to benzothiazoles. 2-Di-alkylamino (alkylmercapto)-6-aminobenzothiazoles were also synthesized.
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Masaki Ohta, Rokuro Sudo
1951 Volume 71 Issue 1 Pages
45-48
Published: January 25, 1951
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Details are given on the syntheses of 3 kinds of sulfone-pyrimidines, viz. 2-Amino-4-methyl-6-
p-aminophenylsulfone-, 2-
p-aminophenylsulfone-4-methyl-6-amino- and 2, 6-di-(
p-aminophenylsulfone)-4-methyl-pyrimidines.
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Masaki Ohta
1951 Volume 71 Issue 1 Pages
48-50
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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Comparative study was made on the behavior and the product of the bromination of
p-nitro-phenoxy-acetone (I),
p-nitrophenylmercapto-acetone (II) and
p-nitrobenzenesulfone-acetone (III). It can be assumed that the formation of bromides and the difference in the properties are due to the difference in the negativity of O, S and SO
2, and to the possession of lone-pair electrons by O and S atoms. The γ-bromides of (I) and (III), and the α-bromide of (II) condense with thioacetamide to form thiazole derivatives.
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Makoto Oda, Minoru Hirano
1951 Volume 71 Issue 1 Pages
51-52
Published: January 25, 1951
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[in Japanese], Yoshio Sakurai, Keishi Yoshino
1951 Volume 71 Issue 1 Pages
53-56
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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[in Japanese]
1951 Volume 71 Issue 1 Pages
57-60
Published: January 25, 1951
Released on J-STAGE: February 19, 2010
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