Reaction of isothiocyanates with thiourea and amidinothioureas: Formation of S-(N-substituted thiocarbamyl)isothioureas and 1-Alkyl(or aryl)-4-imino(or arylimino)-6-iminohexahydro-1,3,5-triazine-2-thiones

Abstract

Alkyl and aryl isothiocyanates react with thiourea in the presence of alkali to yield S-(N-substituted thiocarbamyl)isothioureas. The products are identified by their chemical and mass spectral characteristics.These compounds yield 5-imino-2-alkyl(or ary1)imino-1,3,4-dithiazolidine salts when oxidized in acid medium. The parent compounds are regenerated from these dithiazolidines on reduction with hydrogen sulphide.� Condensation of isothiocyanates with amidinothiourea and aryl amidinothioureas on the other hand yields 1-alkyl(or aryl)-4,6-diiminohexahydro-1,3,5-triazine-2-thiones and 1-alkyl(or ary1)-4-arylimino-6-iminohexahydro-1,3,5-triazine-2-thione respectively.Plausible mechanisms for these reactions are discussed.