Triethylamine → HCID 22473796, compound

Participants

Reaction Steps

Oxalyl chloride (1 ml) was added dropwise under nitrogen at 0° C. to a stirred suspension of 7-methoxybenzo[b]thiophene-2-carboxylic acid (1.9 g) in dichloromethane (25 ml), then dimethylformamide (2 drops) was added and the mixture was stirred at ambient temperature for 4.5 hours. N,O-Dimethylhydroxylamine hydrochloride (1 g), triethylamine (3.2 ml) and dichloromethane (5 ml) were added, the mixture was stirred at ambient temperature for 19 hours, then it was poured into water (60 ml). The product was extracted into dichloromethane (2×30 ml), the combined extracts were dried (MgSO4), and the solvent was removed in vacuo. The residue was purified by flash chromatography over silica using dichloromethane as eluant. Appropriate fractions were combined and the solvent removed in vacuo to give N,7-dimethoxy-N-methylbenzo[b]thiophene-2-carboxamide (1.5 g) as a gum which was used without further purification.

Provenance & Evidence