Reactions of the Iodomethylate of N,N-Dimethylthiobenzamide with Nucleophilic Reagents

Abstract

The reactions of the iodomethylate (I) of N,N-dimethylthiobenzamide with nucleophilic reagents have been examined. The iodomethylate I reacted with sodium ethylmercaptide and potassium cyanide to give N,N-dimethylbenzamide methylethylmercaptol and α-dimethylamino-α-methylthiobenzyl cyanide respectively. When primary amines and the monosodium salts of active methylene compounds were treated with the iodomethy late I, benzamidine hydroiodides and α-dimethylaminobenzylidene derivatives of the active methylene compounds were, respectively, obtained, and methyl mercaptan was eliminated. Further, it has been found that diamines, such as o-phenylenediamine, easily condensed with the iodomethylate I to yield such heterocyclic compoundsas 2-phenylbenzimidazole, while methyl mercaptanand dimethylamine were eliminated.