Ethyl Acetate → N-cyclohexylmethyl-3,4,5-trifluorobenzamide

HRID 601989

Reaction equation

HRID 601989 reaction equation
C(OCC)(=O)C.[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([F:18])[C:16]=1[F:17])[C:11](Cl)=[O:12].[CH:19]1([CH2:25][NH2:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(N(CC)CC)C>[CH:19]1([CH2:25][NH:26][C:11](=[O:12])[C:10]2[CH:9]=[C:8]([F:7])[C:16]([F:17])=[C:15]([F:18])[CH:14]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 76688CyclohexanemethylamineHCID 27770233,4,5-Trifluorobenzoyl chloride

Product 1

HCID 57445689N-cyclohexylmethyl-3,4,5-trifluorobenzamideYield 100.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 10 ml of ethyl acetate were added 0.50 g of 3,4,5-trifluorobenzoyl chloride, 0.32 g of cyclohexylmethylamine and 0.50 g of triethylamine and the mixture obtained was stirred at room temperature for 3 hours. The reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure. Crystals obtained were washed with a mixture of hexane and MTBE to obtain 0.70 g of N-cyclohexylmethyl-3,4,5-trifluorobenzamide. N-cyclohexylmethyl-3,4,5-trifluorobenzamide:

Workup

  1. customthe mixture obtained
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customCrystals obtained
  5. washwere washed with a mixture of hexane and MTBE

Sources & evidence

ORD record
ord-342b219469014e799cdf831ccc754542
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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