Ortho-Selective Nucleophilic Aromatic Substitution Reactions of Polyhaloanilines with Potassium/Sodium O-Ethyl Xanthate: A Convenient Access to Halogenated 2(3H)-Benzothiazolethiones

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.