A one-pot conversion of di-substituted thiourea toO-organyl arylthiocarbamate using FeCl₃

Abstract

Unsymmetrical thiourea, which on demand can generate isothiocyanate in the presence of FeCl₃, can serve as a latent isothiocyanate functionality and circumvent the difficulties associated with the direct use of reactive isothiocyanate functionality. An unusual and unorthodox reactivity has been achieved during a one-pot reaction of an unsymmetrically di-substituted thiourea with an alcohol in the presence of FeCl₃ leading to an expeditious synthesis of O-organyl arylthiocarbamates. In this reaction, a thiono-ester (C‒O) bond is formed at the expense of a thioamidic (C‒N) bond and works over a wide range of structurally diverse thioureas and alcohols without affecting the other functional groups.