2-Tolyl isocyanate → methyl 3-bromo-4-[N'-(2-methylphenyl)ureido]phenylacetate

Participants

Reaction Steps

To a mixture of methyl 4-amino-3-bromophenylacetate (587 mg, 2.40 mmol) and 2-methylphenyl isocyanate (0.287 ml, 2.40 mmol) in THF (2 ml) was added Et3 N (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-methylphenyl)ureido]phenylacetate (650 mg, 72%) as a pale brown powder. 1H-NMR (CDCl3) δ2.34 (s, 3H), 3.53 (s, 2H), 3.68 (s, 3H), 6.18 (br, 1H), 6.96 (br, 1H), 7.18–7.33 (m, 4H), 7.29 (d, J=4.4 Hz, 1H), 7.30 (d, J=7.3 Hz, 1H), 8.19 (d, J=8.3 Hz, 1H); MS (ESI) m/z 377 (M+), 379 (M++2).

Provenance & Evidence