The chemistry of o-phenylene di-isothiocyanate. Part 1. Some reactions with N-nucleophiles

Abstract

Reactions of o-phenylene di-isothiocyanate are described with a variety of nitrogen nucleophiles. Primary and secondary amines and also substituted hydrazines give 1 :1 reaction products, 1-substituted thiocarbamoyl benzimidazoline-2-thiones. Hydrazine gives a 2 : 1 reaction product, to be regarded as a hydrazine salt. The products from primary amines are relatively unstable, yielding isothiocyanates and benzimidazoline-2-thione. Some Schiff bases and derivatives of isoquinoline give rise to thiadiazinobenzimidazoles.