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

HRID 350441

Reaction equation

HRID 350441 reaction equation
[Cl: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[Cl:18])=[O:10].[OH-].[Na+]>C1COCC1>[Cl: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[Cl:18])=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23512406methyl 3-chloro-4-[N'-(2-chlorophenyl)ureido]phenylacetate

Product 1

HCID 235125363-chloro-4-[N'-(2-chlorophenyl)ureido]phenylacetic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-chloro-4-[N′-(2-chlorophenyl)ureido]phenylacetate (1.35 g, 3.82 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 3-chloro-4-[N′-(2-chlorophenyl) ureido]phenylacetic acid (1.12 g, 86%) as colorless powder. 1H-NMR (DMSO-d6) δ 3.52 (s, 2H), 7.05 (m, 1H), 7.17 (d, J=8.5 Hz, 1H), 7.30 (d, J=7.6 Hz, 1H), 7.37 (s, 1H), 7.46 (dd, J=8.0, 1.5 Hz, 1H), 7.95 (dd, J=8.3, 1.2 Hz, 1H), 8.07 (d, J=8.3 Hz, 1H), 9.00 (d, J=8.0 Hz, 2H); MS (FAB) m/z 339 (M++1), 341 (M++3), 343 (M++5).

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-619599869a2446d79e71cbf2233c50e8
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Linked notes

Loading…