Triethylamine → 4-Chloro-2-[3-(2-fluoro-phenyl)-ureido]-benzoic acid

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Reaction Steps

2-Amino-4-chlorobenzoic acid (0.3 g), 2-fluorophenylisocyanate (0.2 ml) and triethylamine (0.24 ml) were stirred in toluene (20 ml) for a week. More 2-fluorophenylisocyanate (0.1 ml) was added and stirring continued for another week. The mixture was concentrated to almost dry, water was added and the pH was adjusted to 1 with diluted HCl. Water was decanted and the residue was dissolved in warm 96% EtOH. The pH was adjusted to 1 again with 4N HCl resulting in the precipitation of a solid, which was filtered and dried to give 4-chloro-2-[3-(2-fluoro-phenyl)-ureido]-benzoic acid (0.25 mg). Mp.=195-197° C. 4-Chloro-2-[3-(3-trifluromethyl-phenyl)-ureido]-benzenesulfonamide (Compound 10):

Provenance & Evidence