Water → HCID 23070362, compound

HRID 1865352Notes

Reaction equation

HRID 1865352 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([OH:30])=[C:11]([CH:29]=1)[C:12]([NH:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1)=[O:13].O>O1CCCC1>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([O:30][C:2]([O:4][CH3:5])=[O:3])=[C:11]([CH:29]=1)[C:12]([NH:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:26])([F:27])[F:28])[CH:16]=1)=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6586Methyl chloroformateHCID 5081913Imd-0354

Product 1

HCID 23070362HCID 23070362, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl chloroformate(42 μL, 0.54 mmol) was added to a solution of 5-chloro-2-hydroxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamide 1 sodium salt(200 mg, 0.49 mmol) in tetrahydrofuran(5 mL) under ice cooling, and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed successively with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was washed with n-hexane under suspension to give the title compound(171.2 mg, 78.6%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the ethyl acetate layer was washed successively with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue obtained by evaporation of the solvent under reduced pressure
  5. washwas washed with n-hexane under suspension

Sources & evidence

ORD record
ord-f88b2be8f56741b6a04ba725ff1eeeba
Source dataset
uspto-grants-2009_12
Patent number
US07626042B2

Reaction notes

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