Anthranilic Acid → 2-{4-[2-(4-Fluoro-phenyl)-ethylcarbamoyl]-benzenesulfonylamino}-benzoic acid

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Reaction Steps

A solution of the title B compound, 4-[2-(4-fluoro-phenyl)-ethylcarbamoyl]-benzene-sulfonyl chloride (171 mg, 0.5 mmol) in THF (2 mL) is added dropwise over 10 min to a solution of the anthranilic acid (68.6 mg, 0.5 mmol) in water (1 mL) containing sodium bicarbonate (126 mg, 1.5 mmol). After stirring for 30 min, the solvent is evaporated under a stream of nitrogen, and water (8 mL) is added. The mixture is stirred for a few min, then filtered. The filtrate is added dropwise to an excess of 1 N aqueous HCl to precipitate a light tan solid. The solid is collected by filtration, washed with water, and dried under vacuum to give 2-{4-[2-(4-fluoro-phenyl)-ethylcarbamoyl]-benzenesulfonylamino}-benzoic acid: m.p. 85-86° C.; ESI-MS 441 [M−1]−.

Provenance & Evidence