著者

巣山 隆之 曽我 卓生 宮内 一憲

出版者

公益社団法人 日本化学会

雑誌

日本化学会誌(化学と工業化学) (ISSN:03694577)

巻号頁・発行日

vol.1989, no.5, pp.884-887, 1989-05-10 (Released:2011-05-30)

参考文献数

19

被引用文献数

10

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It was found that amines added to the N-cyano group on cyanoguanidines in the presence of FeCl3 or ZnCl2 under mild conditions. For example, the reaction of cyanoguanidine [2a] with butylamine, proceeded at room temperature in the presence of FeCl3 to give butylbiguanide [1a] in 99% yield. Similarly, [2a] or N-cyano-N'-phenylguanidine [2b] reacted with diethylamine, benzylamine, hexadecylamine, octadecylamine and aniline at room temperature or under reflux in dioxane or tetrahydrofuran to give the corresponding biguanides [1].In the presence of ZnCl2, [2] and two equivalents of amines were heated in refluxing dioxane. The initial products, biguanides [1]-ZnCl2 complexes, were readily hydrolyzed by aqueous ammonia or amines to give hydropchlorides of [1].When N-substituted-N'-cyano-S-methylisothioureas [3] reacted with primary amines in the presence of FeCl3 or ZnCl2 the addition to the cyano group and the substitution of the methylthio group with amines occurred at the same time to yield the corresponding [1].