On the reaction of 2‐chloroethylisothiocyanate with aromatic amines

Abstract

Abstract The reaction of aromatic amines with 2‐chloroethylisothiocyanate 2 to give 2‐arylaminothiazolines 1 was investigated. The course of this reaction was found to depend on the electronic nature of the amine and the reaction conditions. With arylamines that are relatively electron‐rich, good yields of the thiazolines 1 were obtained. With electron‐poor amines, adducts 4 , in which two equivalents of 2 reacted with the amine, accompanied 1. The relative amounts of 2:1 adducts increased as the arylamine became progressively more electron deficient. With 3,4‐dichloroaniline, the yields of the 2:1 adducts were promoted by the presence of triethylamine.