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

HRID 880664Notes

Reaction equation

HRID 880664 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 to the mixture, which 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. extractionwas 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-4afe28c04a3b4546b8ea2d5d772db178
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Reaction notes

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