Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Reactions of the Iodomethylate of N,N-Dimethylthiobenzamide with Nucleophilic Reagents
Teruaki MukaiyamaTatsuaki YamaguchiHiroyuki Nohira
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1965 Volume 38 Issue 12 Pages 2107-2110

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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.

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