Triethylamine → 3-Amino-5-bromothiophene-2-carboxamide

Participants

Reaction Steps

A mixture of 3-amino-5-bromothiophene-2-carboxylic acid (0.154 g, 0.690 mmol), ammonium chloride (0.369 g, 6.90 mmol), triethylamine (0.964 mL, 6.90 mmol) and DMF (4.0 mL) was stirred for 10 min. Then, 1-hydroxybenzotriazole (0.284 g, 2.10 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.403 g, 2.10 mmol) were added and stirring was continued for 4 days. The mixture was then poured into sat. aqueous sodium hydrogen carbonate (100 mL). Extraction with ethyl acetate (60 mL, 20 mL), washing with brine, drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. This oil was purified by column chromatography (Combiflash, silica gel, hexanes to 90:10 hexanes/ethyl acetate) to afford the title compound (0.118 g, 78%) as a brown oil:

Provenance & Evidence