Thiocyanation of alkylanilines. A simple and efficient synthesis of thiosulfonates containing 2-aminobenzothiazole

Thiocyanation of anilines was used to introduce a thiol functionality and to construct the aminothiazole ring, all in a single step. A systematic study of thiocyanation of alkyl anilines was investigated to understand the regiochemistry of the reaction. X-Ray crystal structures of two 2-aminobenzothiazoles were determined to assign the structures without any ambiguity. The intermediates obtained were further expanded to thiosulfonates containing 2-aminobenzothiazoles, which are extremely valuable intermediates to synthesize HIV protease inhibitors.