HCID 23512268, compound → HCID 23512013, compound

HRID 350431Notes

Reaction equation

HRID 350431 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10](=[O:24])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21]CC)=[O:20])=[CH:14][CH:13]=1>C1COCC1.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10](=[O:24])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 23512268HCID 23512268, compound

Product 1

HCID 23512013HCID 23512013, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of ethyl 4-[N′-(2,6-dichlorophenyl)ureido]phenylacetate (3.19 g, 8.69 mmol) in THF (70 ml), 0.25 N NaOH (70 ml) was added. After stirring at room temperature for 17 h, the solvent was concentrated in vacuo. The residue was triturated by the addition of water, to give 4-[N′-(2,6-dichlorophenyl)ureido]phenylacetic acid (2.44 g, 82%) as colorless powder. mp 262–263° C. (dec.); 1H-NMR (DMSO-d6) δ 3.48 (s, 2H), 7.14 (d, J=8.3 Hz, 2H), 7.31 (t, J=8.3 Hz, 1H), 7.37 (d, J=8.3 Hz, 2H), 7.52 (d, J=8.0 Hz, 2H), 8.18 (s, 1H), 8.90 (s, 1H), 12.22 (br, 1H); MS (ESI) 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 water

Sources & evidence

ORD record
ord-be87960e66bf453dbb9dab42d63e5071
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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