Sodium Hydroxide → 4-[N'-(2-bromophenyl)ureido]-3-chlorophenylacetic acid

HRID 350443Notes

Reaction equation

HRID 350443 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:23])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C)=[O:19])=[CH:13][C:12]=1[Cl:22].[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:23])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][C:12]=1[Cl:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23512063methyl 4-[N'-(2-bromophenyl)ureido]-3-chlorophenylacetate

Product 1

HCID 235123954-[N'-(2-bromophenyl)ureido]-3-chlorophenylacetic acidYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-[N′-(2-bromophenyl)ureido]-3-chlorophenylacetate (1.34 g, 3.37 mmol) in THF (30 ml) was added 0.25 N NaOH (30 ml). After stirring at room temperature for 14 h, the solvent was concentrated in vacuo. The residue was triturated by the addition of 1 N HCl and dried at 60° C. for 2 days under a reduced pressure to give 4-[N′-(2-bromophenyl)ureido]-3-chlorophenylacetic acid (1.03 g, 80%) as colorless powder. 1H-NMR (DMSO-d6) δ 3.56 (s, 2H), 7.00 (m, 1H), 7.17 (dd, J=9.0, 1.7 Hz, 1H), 7.32–7.40 (m, 2H), 7.62 (dd, J=8.0, 1.2 Hz, 1H), 7.95 (m, 2H), 8.83 (s, 1), 9.01 (s, H), 12.41 (br, 1H); MS(FAB) m/z 385 (M++2), 386(M++4), 388 (M++6).

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. customThe residue was triturated by the addition of 1 N HCl
  3. customdried at 60° C. for 2 days under a reduced pressure

Sources & evidence

ORD record
ord-39ede9b407a5402b81d53c5f7b180988
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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