반응 #80574

반응 방정식

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

수율 71.0%

용매

toluene

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to reflux for 84 hours
3. 3
   온도The reaction mixture was cooled
4. 4
   기타the solvent removed under reduced pressure
5. 5
   workup.DISSOLUTIONThe crude residue was redissolved in methylene chloride
6. 6
   세척washed with water, aqueous sodium bicarbonate and brine
7. 7
   기타After drying
8. 8
   여과(Na2SO4), filtration
9. 9
   농축concentrating in vacuo
10. 10
    기타the crude mixture was chromatographed on silica gel

실험 절차

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.

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