Ammonium Hydroxide → 2-amino-N-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)-2-methylpropanamide

Participants

Reaction Conditions

Reaction Steps

A round bottomed flask was charged with 2-bromo-N-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)-2-methylpropanamide (5 g, 12.06 mmol) and a stir bar, followed by tetrahydrofuran (25 mL, 0.5 M) and ammonium hydroxide (30%, 7.82 ml, 60.3 mmol, 5 equiv). The solution was stirred at 60° C. 4 h, at which point LC/MS analysis indicated complete consumption of the starting material. The solution was diluted with ethyl acetate, washed successively with water and brine, and purified by column chromatography (eluting with hexanes/ethyl acetate) to yield 2-amino-N-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)-2-methylpropanamide as a yellow amorphous solid (m/z=351), which was used in the subsequent reaction.

Provenance & Evidence