Chemoselective N-benzoylation of aminophenols employing benzoylisothiocyanates

Abstract

The paper describes the N-benzoylation of 2-aminophenol and 4-aminophenol employing benzoylisothiocyanates in a chemoselective manner. The products N-(2-hydroxyphenyl)benzamides, that are compounds of biological interest, have been identified by simple chemical test, satisfactory analytical and spectral data (IR, 1H and 13C NMR). The formation of product has been explained via the formation of the corresponding thiourea followed by elimination of thiocyanic acid triggered by intramolecular nucleophilic attack of aromatic nitrogen on the carbonyl group of thioureas.