Chlorophenyl isocyanate → tert-butyl 4-[N'-(2-chlorophenyl)ureido]-3-methylphenylacetate

Participants

Reaction Steps

To a stirred mixture of tert-butyl 4-amino-3-methylphenylacetate (1.00 g, 4.52 mmol), 2-chlorophenyl isocyanate (0.55 ml, 4.52 mmol) in THF (10 ml) was added Et3 N (0.13 ml, 0.90 mmol) at room temperature. After 6 h stirring, the reaction mixture was concentrated in vacuo. The residue was triturated by the addition of n-hexane, to give tert-butyl 4-[N′-(2-chlorophenyl) ureido]-3-methylphenylacetate (1.57 g, 93%) as a pale yellow powder. mp 104–106° C. (dec.); 1H-NMR (CDCl3) δ 1.45 (s, 9H), 2.28 (s, 3H), 3.51 (s, 2H), 6.33 (br, 1H), 6.96 (t, J=7.6 Hz, 1H), 7.08 (br, 1H), 7.16–7.30 (m, 4H), 7.42 (m, 1H), 8.2 (d, J=8.1 Hz, 1H).

Provenance & Evidence