Synthesis of 2-Hydroxy-3-(3-substituted thiamido)amino-5-methyl-a-bromoacetophenones

Abstract

2-Hydroxy-3-nitro-5-methyl-a-bromoacetophenone (1) firstly reduced to 2-hydroxy-3-amino- 5-methyl-a-bromoacetophenone (2) with treatment of tin and hydrochloric acid. 2-Hydroxy-3-amino-5-methyl-a-bromoacetophenone (2) is further treated with various isothiocyanate (3) such as phenylisothiocyanate (3a), p-chloro-phenylisothiocyanate (3b), p-tolylisothiocyanate (3c), methylisothiocyanate (3d), ethylisothiocyanate (3e) and t-butylisothiocyanate (3f), in presence of acetone-ethanol medium to synthesize 2-hydroxy-3-(3-substituted thiamido)amino-5-methyl-a-bromoacetophenones (4). The products isolated in these reactions were characterized on the basis of conventional elemental analysis, chemical characteristrics and spectral data.