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Paper | Regular issue | Vol 34, No. 10, 1992, pp.1897-1904
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6095
The Serendipitous Formation of an Unusual Methyl N’-Cyano-N-[5-methylthio-1,2,4-triazol-3-ylidene]carbamimidothioate and Subsequent Reactions

Dennis J. Hlasta,* Malcolm R. Bell, Rudolf K. Kullnig, and Joseph R. Wetzel

*Departments of Medical Chemistry and Molecular Characterization, Sterling Winthrop Pharmaceuticals Research Division, 81 Columbia Turnpike, Rensselaer, New York 12144, U.S.A.

Abstract

Dimethyl cyanocarbamimidodithioate (1) (2 equivalents) reacts with 1,2-dimethylhydrazine to afford the cyclic derivative, methyl N’-cyano-N-(5-methylthio-1,2,4-triazol-3-ylidene)carbamimidothioate (5), instead of an expected acyclic derivative. The triazole (5) undergoes di-addition-elimination reactons with primary aliphatic amines to afford N’’-cyano-N-(5-amino-1,2,4-triazol-3-ylidene)guanidines (6).