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

HRID 52321Notes

Reaction equation

HRID 52321 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][N:13]=[CH:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86750631HCID 86750631, compound

Product 1

HCID 116371511-[4-(methylsulfonyl)phenyl]-1H-imidazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-4-hydroxy-4-[methoxy)methyl]-1-[4-(methylsulfonyl)phenyl]-4,5-dihydro-1H-imidazole from Step 2 (1 mmol) and p-toluenesulfonic acid monohydrate (100 mg) in toluene (70 mL) is heated to reflux for 48 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 chromatographed on silica gel using hexane/ethyl acetate to give 2-(4-chlorophenyl)-4methoxy)methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazole.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 48 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 chromatographed on silica gel

Sources & evidence

ORD record
ord-3375f7d104c74a189744ea1bad619de5
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

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