Ortho-selective nucleophilic aromatic substitution reactions of polyhaloanilines with potassium/sodium o-ethyl xanthate: a convenient access to halogenated 2(3H)-benzothiazolethiones.

Abstract

Polyhaloanilines bearing an ortho halogen atom undergo smooth nucleophilic aromatic substitution reactions with anionic sulfur nucleophiles at relatively mild temperatures (95-120 degrees C). These reactions are very efficient and highly ortho-selective. With potassium/sodium O-ethyl xanthate as a nucleophile, subsequent cyclization follows to afford halogenated 2(3H)-benzothiazolethiones (2-mercaptobenzothiazoles) in high yields.