Reaktion #80596

Reaktionsgleichung

2-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-[(phenylthio)methyl]-4,5-dihydro-1H-imidazole

p-toluenesulfonic acid monohydrate

→

2-(4-chlorophenyl)-4-[(phenylthio)methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazole

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis heated
2. 2
   Temperaturto reflux for 48 hours
3. 3
   TemperaturThe reaction mixture is cooled
4. 4
   Sonstigethe solvent removed under reduced pressure
5. 5
   workup.DISSOLUTIONThe crude residue is redissolved in methylene chloride
6. 6
   Waschenwashed with water, aqueous sodium bicarbonate and brine
7. 7
   SonstigeAfter drying
8. 8
   Filtration(Na2SO4), filtration and concentration in vacuo
9. 9
   Sonstigethe crude mixture is chromatographed on silica gel

Vorschrift

A mixture of 2-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-[(phenylthio)methyl]-4,5-dihydro-1H-imidazole (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)-4-[(phenylthio)methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazole.

Quelle