Synthesis of thioamides from nitriles in 1,4-dioxane by using CH3SO3H and thioacetamide

Abstract

A method for the preparation of thioamides from nitriles using CH₃SO₃H and thioacetamide is described. Using this method, nitriles including aromatic nitriles, aromatic heterocyclic nitrile and aliphatic nitriles were converted into the corresponding thioamides in moderate to good yields. The reaction proceeded smoothly at reflux temperature in 1,4-dioxane, with reaction times ranging from 8 to 12 hours. Functional groups including halogen, nitro, alkoxy, hydroxy, ester, and acyl remained unaltered, indicating good chemoselectivity. Thioacetamide reacts with nitriles in the presence of CH₃SO₃H to yield acetonitrile, as deduced from experimental evidence.