Benzoyl chloride, 3-chloro- → 5-(3-Chloro-benzoylamino)-2-phenoxy-benzoic acid methyl ester

HRID 1967645Notes

Reaction equation

HRID 1967645 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24]>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([NH:10][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([Cl:19])[CH:21]=2)[CH:7]=[CH:6][C:5]=1[O:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 23019285Benzoic acid, 5-amino-2-phenoxy-, methyl ester

Product 1

HCID 592023865-(3-Chloro-benzoylamino)-2-phenoxy-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

5-Amino-2-phenoxy-benzoic acid methyl ester (972 mg, 4.00 mmol) (prepared according to WO 01/046171) was dissolved in a biphasic mixture of ethyl acetate (10 ml) and aqueous sodium bicarbonate (1N) (10 ml). 3-Chloro-benzoylchloride (770 μl, 6 mmol) was added under vigorous stirring. The mixture was stirred for 18 hours at ambient temperature. The phases were separated, the organic phase was dried over sodium sulfate and concentrated. The residue was used without further purification.

Workup

  1. customThe phases were separated
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was used without further purification

Sources & evidence

ORD record
ord-8b91f7a28a1c41e3b3e3543688163ef0
Source dataset
uspto-grants-2013_04
Patent number
US08420855B2

Reaction notes

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