Triethylamine → methyl 3-bromo-4-[N'-(2-chlorophenyl)ureido]phenylacetate

Participants

Reaction Steps

To a mixture of methyl 4-amino-3-bromophenylacetate (587 mg, 2.40 mmol) and 2-chlorophenyl isocyanate (0.29 ml, 2.40 mmol) in THF (2 ml) was added Et3N (33 ml, 0.24 mmol) at room temperature. After 21 h stirring, the reaction mixture was concentrated in vacuo. The residue was triturated by the addition of n-hexane to give methyl 3-bromo-4-[N′-(2-chlorophenyl)ureido]phenylacetate (710 mg, 74%) as a pale brown powder. 1H-NMR (CDCl3) δ3.57 (s, 2H), 3.70 (s, 3H), 7.02-7.28 (m, 2H), 7.36 (d, J=6.8 Hz, 1H), 7.48 (s, 1H), 8.00-8.11 (m, 2H); MS (ESI) m/z 397 (M+), 399 (M++2), 401 (M++4).

Provenance & Evidence