Reacción #80574

Ecuación de reacción

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

p-toluenesulfonic acid monohydrate

→

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

Rendimiento 71.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturato reflux for 84 hours
3. 3
   TemperaturaThe reaction mixture was cooled
4. 4
   Otrothe solvent removed under reduced pressure
5. 5
   workup.DISSOLUTIONThe crude residue was redissolved in methylene chloride
6. 6
   Lavadowashed with water, aqueous sodium bicarbonate and brine
7. 7
   OtroAfter drying
8. 8
   Filtración(Na2SO4), filtration
9. 9
   Concentraciónconcentrating in vacuo
10. 10
    Otrothe crude mixture was chromatographed on silica gel

Procedimiento

A mixture of 2-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole from Example 1 (6.2 g, 15.4 mmol) and p-toluenesulfonic acid monohydrate (0.9 g, 4.7 mmol) in toluene (300 mL) was heated to reflux for 84 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 concentrating in vacuo, the crude mixture was chromatographed on silica gel using hexane/ethyl acetate (1/1) to give pure 2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazole (4.21 g, 71%) as a white solid: mp (DSC) 183° C. Anal. Calc'd. for C17H12N2SO2F3Cl: C, 50.94, H, 3.02, N, 6.99. Found: C, 50.64, H, 3.03, N, 6.85.

Fuente