Reaktion #80589

Reaktionsgleichung

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

p-toluenesulfonic acid monohydrate

→

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

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux for 48 hours
3. 3
   TemperaturThe reaction mixture was cooled
4. 4
   Sonstigethe solvent removed under reduced pressure
5. 5
   workup.DISSOLUTIONThe crude residue was 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 was chromatographed on silica gel

Vorschrift

A mixture of 2-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-[(4-chlorophenoxy)methyl]-4,5-dihydro-1H-imidazole from Step 3 (750 mg, 1.5 mmol) and p-toluenesulfonic acid monohydrate (135 mg) in toluene (100 mL) was heated to reflux for 48 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 was chromatographed on silica gel using hexane/ethyl acetate (1/1) to give 2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-4-[(4-chlorophenoxy)methyl]-1H-imidazole as a white solid: mp (DSC) 173° C. Anal. Calc'd for C23H18N2Cl2SO3.0.25 H2O: C, 57.81; H, 3.90; N, 5.86; Cl, 14.84. Found: C, 57.67; H, 3.83; N, 5.52; Cl, 15.17.

Quelle