Thionyl Chloride → HCID 18544091, compound

Participants

Reaction Steps

A benzene (30 ml) solution containing 3 g (12.5 mmol) of 3-heptyloxybenzoic 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 2.50 g (14.5 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 3.00 g (yield: 60.0%) of the title compound. NMR (DMS-d6) δ: 0.87 (3 H, t, J=7 Hz), 1.22-1.50 (8 H, m), 1.70-1.80 (2 H, M), 4.41 (2 H, t, J=7 Hz), 7.17-7.23 (1 H, m), 7.33 (1 H, ddd, J=8 Hz, 8 Hz, 2 Hz), 7.77 (2 H, s), 7.90 (1 H, dd, J=8 Hz, 2 Hz), 8.48 (1 H, d, J=8 Hz), 10.38 (1 H, s)

Provenance & Evidence