Abstract
Free acids of cyanoaminocarbonic acid derivatives were observed to be extremely reactive. In this paper, some reactions of methylmercaptocarbonyl-cyanamide (MCC) were investigated.
When an aqueous solution of MCC was allowed to stand at room temperature, di- (methylmercaptocarbonyl) -amide (3) and di- (methylmercaptocarbonyl) -cyanamide (4) were isolated, At elevated temperature MCC was hydrolyzed at the mercaptocarbonyl group to give cyanamide in good yield. On the other hand in the presence of acid the cyano group was selectively hydrated and methylmercapto-carbonyl-urea (5) was obtained. In alcoholic solutions an ester exchainging reaction occurred. The reaction of MCC with aniline was found to proceed stepwise, that is, N-phenyl-N' methylmercaptocarbonyl-guanidine (8) was obtained at room temperature, while N-phenyl-N'-phenylcarbamoyl-guanidine (7) was yielded in hot alcohol. Reaction mechanisms were also discussed in connection with the structure of MCC.
