2-(4-Chlorophenyl)cyclohexan-1-one → 1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid [2-(4-chlorophenyl)-cyclohex-1-enyl]-amide

HRID 1929523Notes

Reaction equation

HRID 1929523 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=O)=[CH:4][CH:3]=1.[CH3:15][N:16]1[CH:20]=[C:19]([C:21]([NH2:23])=[O:22])[C:18]([C:24]([F:27])([F:26])[F:25])=[N:17]1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[NH:23][C:21]([C:19]2[C:18]([C:24]([F:25])([F:27])[F:26])=[N:17][N:16]([CH3:15])[CH:20]=2)=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 38395662-(4-Chlorophenyl)cyclohexan-1-oneHCID 223740641-Methyl-3-(trifluoromethyl)pyrazole-4-carboxamide

Product 1

HCID 236608471-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid [2-(4-chlorophenyl)-cyclohex-1-enyl]-amideYield 57.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

0.521 g 2-(4-chlorophenyl)-cyclohexanone (prepared as described in J. Org. Chem. 70, 2005, page 2967) and 0.482 g 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid amide were suspended with 5 mg p-toluenesulfonic acid in 20 ml toluene and heated to reflux temperature of the solvent for 24 hours under continuos removal of water. The reaction mixture was washed with 5% sodium bicarbonate and water, dried and the solvent was removed under vacuum. The reaction product was purified by chromatography on a silica gel column (eluent: ethylacetate:hexane 1:1). 0.55 g 1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid [2-(4-chlorophenyl)-cyclohex-1-enyl]-amide was obtained in the form of crystals (m.p. 145-148° C.).

Workup

  1. temperatureheated
  2. temperatureto reflux temperature of the solvent for 24 hours
  3. customunder continuos removal of water
  4. washThe reaction mixture was washed with 5% sodium bicarbonate and water
  5. customdried
  6. customthe solvent was removed under vacuum
  7. customThe reaction product was purified by chromatography on a silica gel column (eluent: ethylacetate:hexane 1:1)

Sources & evidence

ORD record
ord-8fa39c899793425291b3817530068a2b
Source dataset
uspto-grants-2012_05
Patent number
US08188088B2

Reaction notes

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