Vitamin B1及び諸関係化合物の研究 第30報
N-置換Thiothiazolone (2) 化合体及びVitamin B1同族体の生成に関する研究 その4
1952 年 72 巻 3 号 p. 366-368
詳細
1952 年 72 巻 3 号 p. 366-368
Condensation of valeroamidine (II) and ethoxymethylene malondinitrile (III) or of valeroimino ether (V) and aminomethylene malondinitrile (VI) yields 2-butyl-4-amino-5-cyanopyrimidine (IV), electrolytic reduction of which, using palladium-black as the cathode, results in the formation of 2-butyl-4-amino-5-aminomethylpyrimidine (VII). Condensantion of (VII) with γ-aceto-γ-chloropropyl alcohol (VIII), in the presence of carbon disulfide and ammonia, gives α-aceto-γ-hydroxypropyl N-[2-butyl-4-aminopyri-midyl (5)]-methyldithiocarbamate (IX) which, when treated with caustic alkali, changes to 2-thio-7-butyl-1, 2, 3, 4-tetrahydropyrimido- (4.5-d) -pyrimidine (X), but heating the diluted hydrochloric acid solution of (IX) results in the formation of 3-[2′-butyl-4′-aminopyrimidyl (5′)]-methyl-4-methyl-5-β-hydroxyethylthiothiazolone (2) (XI). Oxidation of (XI) with hydrogen peroxide in acid medium, followed by treatment with barium chloride yields 3-[2′-butyl-4′-aminopyrimidyl (5′)]-methyl-4-methyl-5-β-hydroxyethyl-thiazolium chloride hydrochloride (1).
