Hydrochloric Acid → [4-({[2-(Trifluoromethyl)phenyl]carbamoyl}amino)phenyl]acetic acid

Participants

Reaction Steps

To a stirred solution of ethyl 4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetate (1.93 g, 5.27 mmol) in THF (10 ml) was added 1 N NaOH (10 ml) and the reaction mixture was heated under reflux for 5 hr. After cooled to room temperature, the mixture was poured into ice-1 N HCl. The resulting precipitate was collected under a reduced pressure and the crude solid was recrystallized from MeOH—CHCl3-IPE to give 4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetic acid (910 mg, 51%) as a white crystalline powder. mp 224–225° C.; 1H-NMR (DMSO-d6) δ 3.50 (s, 2 H), 7.18 (d, J=8.3 Hz, 2 H), 7.25–7.29 (m, 1 H), 7.40 (d, J=8.3 Hz, 2 H), 7.62–7.69 (m, 2 H), 7.95–7.97 (m, 1 H), 8.06 (s, 1 H), 9.37 (s, 1 H), 12.27 (br s, 1 H); Anal. Calcd for C16H13F3N2O3: C, 56.81; H, 3.87; N, 8.28; F, 16.85. Found: C, 56.68; H, 3.87; N, 8.16; F, 16.89.

Provenance & Evidence