An unexpected result of the reaction of benzothioamide derivatives with 2-aryl-2-bromoacetonitriles

Abstract

Unexpectedly, in the reaction of 2-bromo-2-phenylacetonitrile derivatives with 2 mol-equiv. of benzothioamide in DMSO, 3,5-diaryl-1,2,4-thiadiazoles were obtained in excellent yields (83-90%) and in short reaction times (5-10 min). It is found that, in DMF, a quite different reaction takes place and 2,5-diaryl-1,3-thiazol-4-amines are formed as the main products. Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.