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

HRID 354385Notes

Reaction equation

HRID 354385 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[Br:13].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23].CCN(CC)CC>C1COCC1>[Br:13][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][C:22]([NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[Cl:14])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76833Chlorophenyl isocyanateHCID 15462911Methyl 2-(4-amino-3-bromophenyl)acetate

Product 1

HCID 23511959methyl 3-bromo-4-[N'-(2-chlorophenyl)ureido]phenylacetateYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was triturated by the addition of n-hexane

Sources & evidence

ORD record
ord-004bc7f180d24691a25f9395de71d068
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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