Triethylamine → 3-Iodo-N-methoxy-N-methylbenzamide

Participants

Reaction Steps

3-Iodobenzoic acid (3.01 g, 12.1 mmol) was dissolved in DMF (30 mL), and HOBt.H2O (2.45 g, 18.1 mmol), WSC.HCl (3.02 g, 15.8 mmol), N,O-dimethylhydroxylamine hydrochloride (1.30 g, 13.3 mmol), and triethylamine (1.86 mL, 14.6 mmol) were added thereto, and then, the mixture was stirred at room temperature for 4 hours. Water (60 mL) was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine, and then, dried over anhydrous sodium sulfate. Then, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel flash column chromatography (ethyl acetate/n-heptane=100/0 to 50/50) to give 3-iodo-N-methoxy-N-methylbenzamide (3.23 g, yield: 82%).

Provenance & Evidence