Hydrochloric Acid → 4-Phenylsulfonamidocarbonyl-2,6-dimethyl-benzoic acid

Participants

Reaction Conditions

Reaction Steps

2,6-Dimethyl-1,4-benzenedicarboxylic acid (from Preparation 7) (500 mg, 2.6 mmol) and benzene sulfonamide (486 mg, 3.1 mmol) were combined in dry DMF (25 mL), and EDCI (494 mg, 2.6 mmol) was then added with stirring at 0° C. The mixture was stirred for 2 hours at 0° C. and 2 days at room temperature, then 1N HCl (10 mL) was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with 1N HCl (1×), water (5×), and brine (3×); dried (Na2SO4); and rotary evaporated to give the crude product (used as such in the next step) as a white solid; NMR (acetone-d6) showed 8.0-7.4 ppm (multiplet with a singlet at 7.7 ppm, 7H) and 2.4 ppm (singlet, 6H).

Provenance & Evidence