Triethylamine → 3-(N,N-Diethylaminosulfonyl)-N-methoxy-N-methylbenzamide

Participants

Reaction Steps

3-(N,N-diethylaminosulfonyl)benzoic acid (1.17 g, 4.55 mmol) and N,O-dimethylhydroxylamine hydrochloride (498 mg, 5.11 mmol) were dissolved in CH2Cl2 (30 mL). To this solution was added triethylamine (1.9 mL, 14 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (970 mg, 5.06 mmol) and 4-(N,N-dimethylamino)pyridine (117 mg, 0.958 mmol). The resulting solution was stirred at room temperature for 17 h then poured into saturated aqueous NaHCO3 and extracted 3× with ethyl acetate. The combined organics were washed with brine then dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 70:30 hexanes:acetone) to yield 522 mg of the title compound.

Provenance & Evidence