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

HRID 354388Notes

Reaction equation

HRID 354388 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[Br: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[Br:18])=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23512452methyl 3-bromo-4-[N'-(2-bromophenyl)ureido)phenylacetate

Product 1

HCID 693328483-bromo-4-[N'-(2-bromophenyl)ureido]phenylacetic acidYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-bromo-4-[N′-(2-bromophenyl)ureido]phenylacetate (770 mg, 1.74 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-bromophenyl) ureido]phenylacetic acid (702 mg, 94%) as colorless powder. 1H-NMR (DMSO-d6) δ3.56 (s, 2H), 6.99 (dt, J=7.8, 1.5 Hz, 1H), 7.21 (dd, J=8.3, 1.7 Hz, 1H), 7.33 (dt, J=7.1, 1.5 Hz, 1H), 7.53 (d, J=1.7 Hz, 1H), 7.62 (dd, J=8.1, 1.5 Hz, 1H), 7.82 (d, J=8.3 Hz, 1H), 7.93 (dd, J=8.1, 1.5 Hz, 1H), 8.82 (s, 1H), 8.86 (s, 1H), 12.39 (s, 1H); MS (ESI) m/z 428 (M++1), 430 (M++3).

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-0120991025414537a6d55e8979c8e371
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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