p-Toluenesulfonic acid monohydrate → 1-[4-(Methylsulfonyl)phenyl]-2-(4-chlorophenyl)-4-(trifluoromethyl)-1H-imidazole

HRID 1352924노트

반응식

HRID 1352924 반응식
[Cl: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>[Cl: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:25])=[O:26])=[CH:20][CH:19]=3)[CH:10]=[C:11]([C:13]([F:16])([F:14])[F:15])[N:12]=2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 105740772-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole

생성물 1

HCID 105011901-[4-(Methylsulfonyl)phenyl]-2-(4-chlorophenyl)-4-(trifluoromethyl)-1H-imidazole수율 71%

시약·촉매·용매 1

HCID 1140Toluene용매

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 purified by chromatography 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.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 84 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
  9. concentrationconcentrating in vacuo
  10. customthe crude mixture was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-d72e21489256441684d861b53ee7f8b0
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220770B2

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