2-(Trifluoromethyl)phenyl isocyanate → ethyl 4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetate

Participants

Reaction Steps

To a stirred solution of ethyl 4-aminophenylacetate (1.13 g, 6.31 mmol) and Et3 N (965 ml, 6.92 mmol) in THF (10 ml) was added 2-trifluoromethylphenyl isocyanate (953 ml, 6.31 mmol) and the reaction mixture was stirred at room temperature for 2 days. Resulting precipitate was collected under a reduced pressure and the filtrate was washed with n-hexane to give ethyl 4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetate (1.93 g, 84%) as white needles. mp 137–139° C.; 1H-NMR (CDCl3) δ 1.25–1.29 (m, 3 H), 3.59 (s, 2 H), 4.15–4.20 (m, 2 H), 7.05 (br s, 1 H), 7.13–7.23 (m, 6 H), 7.47–7.51 (m, 1 H), 7.54–7.56 (m, 1 H), 8.01–8.03 (m, 1 H).

Provenance & Evidence