A Safer and Convenient Synthesis of Sulfathiazole for Undergraduate Organic and Medicinal Chemistry Classes

Abstract

A safer method for the synthesis of the sulfonamide drug sulfathiazole, for undergraduate classes, is described. This method improves upon procedures currently followed in several undergraduate teaching laboratories for the synthesis of sulfathiazole. Key features of this procedure include the total exclusion of pyridine, which has potential health hazards, from the first step of the synthesis and a simplified procedure for converting the intermediate p-acetamidobenzenesulfonamide to the final product by acid hydrolysis. Characterization of the synthetic sulfathiazole obtained by the modified route was achieved using MS, NMR, and antibacterial activity testing of the synthetic product against Escherichia coli DH5α.