p-Toluenesulfonic acid monohydrate → 1-(4-Methanesulfonyl-phenyl)-2-p-tolyl-4-trifluoromethyl-1H-imidazole

HRID 1352960

반응식

HRID 1352960 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[CH2:10][C:11](O)([C:13]([F:16])([F:15])[F:14])[N:12]=2)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[CH:10]=[C:11]([C:13]([F:15])([F:16])[F:14])[N:12]=2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 105249012-(4-methylphenyl)-4-hydroxy-1-(4-(methylsulfonyl)phenyl]-4-trifluoromethyl-4,5-dihydro-1H-imidazole

생성물 1

HCID 101997641-(4-Methanesulfonyl-phenyl)-2-p-tolyl-4-trifluoromethyl-1H-imidazole수율 54%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 2-(4-methylphenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-4,5-dihydro-1H-imidazole (Step 2) (0.9 g, 2.3 mmol) and p-toluenesulfonic acid monohydrate (150 mg) in toluene (100 mL) was heated to reflux for 72 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 purified by chromatography on silica gel using toluene/ethyl acetate (1/1) to give pure 2-(4-methylphenyl)-1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazole (462. mg, 54%) as a white solid: mp (DSC) 190° C. Anal. Calc'd for C18H15N2F3SO2: C, 56.84; H, 3.97; N, 7.36; S, 8.43. Found: C, 56.66; H, 3.82; N, 7.23; S, 8.45.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 72 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe crude residue was redissolved in methylene chloride
  6. washwashed with water, aqueous sodium bicarbonate and brine
  7. customAfter drying
  8. filtration(Na2SO4), filtration and concentration in vacuo
  9. customthe crude mixture was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-464b8496e0a943ada5653bb15d0fd545
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220770B2

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