Dimethylamine → 3-(Dimethylcarbamoyl)-4-methoxybenzene-1-sulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-(chlorosulfonyl)-2-methoxybenzoic acid (1.243 g, 4.96 mmol) in dry DCM (20 ml) cooled to 0° C., (COCl)2 (1.302 ml, 14.88 mmol) was added drop-wise followed by few drops of dry DMF and the reaction was stirred at RT for 1 hour. The mixture was concentrated under reduced pressure, treated with dry toluene (30 ml×2) and evaporated to dryness. The residue was suspended in dry toluene (20 ml) and the resulting suspension was cooled to 0° C.; a solution of dimethylamine 2.0 M in THF (4.96 ml, 9.92 mmol) was added drop-wise and the reaction was stirred at RT overnight. The mixture was diluted with DCM and washed with brine; the organic phase was dried over sodium sulfate and the solvent was removed. The crude was purified by flash chromatography on silica gel (EtOAc/petroleum ether=60/40) to give 3-(dimethylcarbamoyl)-4-methoxybenzene-1-sulfonyl chloride (Int. 9) (400 mg, 1.440 mmol, MS/ESI+278.0 [MH]+).

Provenance & Evidence