Thionyl Chloride → 3-Cyclohexylmethoxy-N-(2-sulfamoylphenyl)benzamide

Participants

Reaction Steps

A benzene (30 ml) solution containing 3.00 g (12.8 mmol) of 3-cyclohexylmethoxybenzoic acid and 3 ml of thionyl chloride was heated under reflux for 2 hours and then the solvent was evaporated under a reduced pressure. The resulting residue was dissolved in methylene chloride (30 ml), this solution was added dropwise under ice-cooling to a pyridine (50 ml) solution containing 2.43 g (14.1 mmol) of 2-aminobenzenesulfonamide, the mixture was stirred at room temperature for 18 hours and then methylene chloride was evaporated under a reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with a 1 n hydrochloric acid aqueous solution, water and saturated brine in that order and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The thus obtained crude crystals were recrystallized from acetonitrile to obtain 2.80 g (yield: 56.0%) of the title compound NMR (CDCl3) δ: 1.00-1.39 (5 H, m), 1.68-1.90 (6 H, m), 3.82 (2 H, d J=7 Hz), 4.95 (2 H, s), 7.10 (1 H, ddd, J=8 Hz, 2 Hz, 1 Hz), 7.25 (1 H, ddd, J=8 Hz, 8 Hz, 1 Hz), 7.38 (1 H, dd, J=8 Hz, 8 Hz), 7.45-7.50 (2 H, m), 7.62 (1 H, ddd, J=8 Hz, 8 Hz, 2 Hz), 7.96 (1 H, dd, J=8 Hz, 2 Hz), 8.53 (1 H, dd, J=8 Hz, 1 Hz), 10.03 (1 H, s)

Provenance & Evidence