p-Toluenesulfonic acid monohydrate → HCID 11794411, compound

HRID 52298Notes

Reaction equation

HRID 52298 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][C:11](O)([C:13]([F:16])([F:15])[F:14])[N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([F:16])([F:14])[F:15])[N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 107398551-(4-fluorophenyl)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole

Product 1

HCID 11794411HCID 11794411, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole (Example 3) (770 mg, 1.9 mmol) and p-toluenesulfonic acid monohydrate (88 mg) in toluene (80 mL) was heated to reflux for 20 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude residue was redissolved in methylene chloride and washed with water, aqueous sodium bicarbonate and brine. After drying (Na2SO4), filtration and concentration in vacuo, the crude mixture (520 mg) was chromatographed on silica gel using hexane/ethyl acetate (1/1) to give pure 1-(4-fluorophenyl)-2-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazole (328 mg, 44%) as a white solid: mp (DSC) 183° C. Anal. Calc'd. for C17H12N2SO2F4 : C, 53.13, H, 3.15, N, 7.29. Found: C, 53.20, H, 3.22, N, 7.18.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe crude residue was 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 (520 mg) was chromatographed on silica gel

Sources & evidence

ORD record
ord-dd80bda6141f457a8b6dc125575f425a
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

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