p-Toluenesulfonic acid monohydrate → 1-[4-(methylsulfonyl)phenyl]-2-(4-trifluoromethylphenyl)-4-trifluoromethyl-1H-imidazole

HRID 1166350Notes

Reaction equation

HRID 1166350 reaction equation
O[C:2]1([C:27]([F:30])([F:29])[F:28])[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[C:4]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)=[N:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:16][S:13]([C:10]1[CH:11]=[CH:12][C:7]([N:5]2[CH:6]=[C:2]([C:27]([F:28])([F:29])[F:30])[N:3]=[C:4]2[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=2)=[CH:8][CH:9]=1)(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22997716HCID 22997716, compound

Product 1

HCID 229977101-[4-(methylsulfonyl)phenyl]-2-(4-trifluoromethylphenyl)-4-trifluoromethyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-hydroxy-1-[4-(methylsulfonyl)phenyl]-2-(4-trifluoromethylphenyl)-4-trifluoromethyl-4,5-dihydro-1H-imidazole (10 mmol) and p-toluenesulfonic acid monohydrate (1 mmol) in toluene (100 mL) is heated to reflux for 72 hours. The reaction mixture is cooled and the solvent removed under reduced pressure. The crude residue is redissolved in methylene chloride and washed with water, aqueous sodium bicarbonate and brine. After drying (Na2SO4), filtration and concentration in vacuo, the crude mixture is purified by chromatography on silica gel using toluene/ethyl acetate to give pure 1-[4-(methylsulfonyl)phenyl]-2-(4-trifluoromethylphenyl)-4-trifluoromethyl-1H-imidazole.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 72 hours
  3. temperatureThe reaction mixture is cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe crude residue is redissolved in methylene chloride
  6. washwashed with water, aqueous sodium bicarbonate and brine
  7. customAfter drying
  8. filtration(Na2SO4), filtration and concentration in vacuo
  9. customthe crude mixture is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-fc44475b9ad7450998d2bfc378009865
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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