Water → N-(4-Bromo-2-chloro-6-trifluoromethyl-phenyl)-3-cyclopentyl propionamide

HRID 2067782Notes

Reaction equation

HRID 2067782 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8](Cl)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:11][C:12]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[C:15]([NH2:16])=[C:14]([Cl:23])[CH:13]=1.O>C(#N)C>[Br:11][C:12]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[C:15]([NH:16][C:8](=[O:9])[CH2:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:14]([Cl:23])[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 660393-Cyclopentylpropionyl chlorideHCID 162179374-Bromo-2-chloro-6-(trifluoromethyl)aniline

Product 1

HCID 58097325N-(4-Bromo-2-chloro-6-trifluoromethyl-phenyl)-3-cyclopentyl propionamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Cyclopentyl propionyl chloride (1.28 g, 8.0 mmol) was added to a solution of 4-bromo-2-chloro-6-(trifluoromethyl)aniline (2.0 g, 7.3 mmol) in acetonitrile (10 mL). The reaction mixture was stirred at room temperature overnight. Water was added, and the mixture was then extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. Purification by column chromatography (100% DCM) afforded the title compound as a powder.

Workup

  1. extractionthe mixture was then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customPurification by column chromatography (100% DCM)

Sources & evidence

ORD record
ord-20cb7e864b24453b9f8406c6bb4b1b28
Source dataset
uspto-grants-2012_10
Patent number
US08293911B2

Reaction notes

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