Hydrochloric Acid → HCID 86745150, compound

Participants

Reaction Steps

4-Methoxycarbonyl-benzoic acid (from Preparation 11) (5.0 g, 28 mmol) was dissolved in 100 mL of anhydrous dichloromethane. After the addition of DMAP (3.39 g, 28 mmol) and benzenesulfonamide (4.36 g, 28 mmol), EDCI (5.85 g, 31 mmol) was gradually added to the stirred mixture. After 18 hours at room temperature, rotary evaporation of the mixture gave a residue which was mixed with ethyl acetate and 1 N HCl. The organic phase was washed with water (1×) and brine (2×), dried (Na2SO4), rotary evaporated, and dried at high volume to afford 8.7 g (98%) of methyl 4-phenylsulfonamido-carbonyl-benzoate (4-C6H5SO2 --NHCO--C6H4 --COOCH3) as a white solid. A solution of this material (3.2 g, 10 mmol) in 130 mL of dioxane/water (3:1) was cooled to 0° C. 1 N Sodium hydroxide was added dropwise, followed by vigorous stirring at 0° C. for 20 minutes, then at room temperature for 2 hours. The mixture was again cooled to 0° C., and then acidified to pH 2 by gradual addition of 1 N HCl. The mixture was rotary evaporated, and the aqueous residue was extracted with ethyl acetate (3×). The combined extracts were washed with brine, dried (Na2SO4), rotary evaporated, and dried at high vacuum to afford the product (4-C6H5SO2NHCO--C6H4 --COOH), m.p. 267°-270° C.

Provenance & Evidence