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

HRID 350449Notes

Reaction equation

HRID 350449 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]>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

4

Reactant 2

HCID 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 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-chlorophenyl)ureido]phenylacetate (710 mg, 74%) as a pale brown powder. 1H-NMR (CDCl3) δ 3.57 (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. additionwas added Et3 N (33 ml, 0.24 mmol) at room temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue was triturated by the addition of n-hexane

Sources & evidence

ORD record
ord-ecf37e9c71e54ad38220501df6c3a043
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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