Reacción #80599

Ecuación de reacción

1-[4-(methylsulfonyl)phenyl]-4,5-dihydro-1H-imidazole

p-toluenesulfonic acid monohydrate

→

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

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais heated
2. 2
   Temperaturato reflux for 48 hours
3. 3
   TemperaturaThe reaction mixture is cooled
4. 4
   Otrothe solvent removed under reduced pressure
5. 5
   workup.DISSOLUTIONThe crude residue is redissolved in methylene chloride
6. 6
   Lavadowashed with water, aqueous sodium bicarbonate and brine
7. 7
   OtroAfter drying
8. 8
   Filtración(Na2SO4), filtration and concentration in vacuo
9. 9
   Otrothe crude mixture is chromatographed on silica gel

Procedimiento

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.

Fuente