Sodium Hydroxide → 3-bromo-4-[N'-(2-methylphenyl)ureido]phenylacetic acid

HRID 350448Notes

Reaction equation

HRID 350448 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:19][C:20]([O:22]C)=[O:21])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])=[O:10].[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:19][C:20]([OH:22])=[O:21])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23512369methyl 3-bromo-4-[N'-(2-methylphenyl)ureido]phenylacetate

Product 1

HCID 235121223-bromo-4-[N'-(2-methylphenyl)ureido]phenylacetic acidYield 195.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-bromo-4-[N′-(2-methylphenyl)ureido]phenylacetate (650 mg, 1.72 mmol) in THF (10 ml) was added 0.25 N NaOH (10 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 3-bromo-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (1.22 g, 100%) as colorless powder. 1H-NMR (DMSO-d6) δ 2.26 (s, 3H), 3.32 (s, 2H), 6.93 (m, 2H), 7.10–7.17 (m, 4H), 7.76 (d, J=8.1 Hz, 2H), 8.52 (s, 1H); MS (ESI) m/z 385 (M++Na), 387 (M++2+Na).

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-c898a9e13d7b4d43a3fef6c7ec4f9e72
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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