Phenyl isocyanate → ethyl 4-(N'-phenylureido)phenylacetate

Participants

Reaction Steps

To a stirred solution of ethyl 4-aminophenylacetate (6.43 g, 35.9 mmol) and Et3N (5.50 ml, 39.5 mmol) in THF (70 ml) was added phenyl isocyanate (3.90 ml, 35.9 mmol), and the reaction mixture was stirred at room temperature for 4 days. Resulting precipitate was collected under a reduced pressure and the filtrate was washed with n-hexane to give ethyl 4-(N′-phenylureido)phenylacetate (9.64 g, 90%) as a white crystalline powder. mp 153-155° C.; 1H-NMR (CDCl3) δ1.26 (t, J=7.1 Hz, 3 H), 3.52 (s, 2 H), 4.15 (q, J=7.1 Hz, 2 H), 6.98-7.04 (m, 1 H), 7.07-7.11 (m, 4 H), 7.18-7.25 (m, 5 H), 7.42 (s, 1 H); MS (FAB) m/z 299 (M++1); Anal. Calcd. for C17H18N2O3: C, 68.44; H, 6.08; N, 9.39. Found: C, 68.22; H, 6.10; N, 9.36.

Provenance & Evidence