p-Toluenesulfonic acid monohydrate → 1h-Imidazole,2-(3-chloro-4-methylphenyl)-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-

HRID 1166330노트

반응식

HRID 1166330 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[CH2:11][C:12](O)([C:14]([F:17])([F:16])[F:15])[N:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][CH:20]=3)[CH:11]=[C:12]([C:14]([F:17])([F:15])[F:16])[N:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 117970112-(3-chloro-4-methylphenyl)-4-hydroxy-1-(4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole

생성물 1

HCID 105019571h-Imidazole,2-(3-chloro-4-methylphenyl)-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-수율 95%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 2-(3-chloro-4-methylphenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole from Step 2 (725 mg, 1.7 mmol) and p-toluenesulfonic acid monohydrate (150 mg) in toluene (40 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 (860 mg) was purified by chromatography on silica gel using toluene/ethyl acetate 1/1 to give pure 2-(3-chloro-4-methylphenyl)-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazole (660 mg, 95%) as a white solid: mp(DSC) 206° C. Anal. Calc'd. for C18H14N2SO2F3Cl: C, 52.12, H, 3.40, N, 6.75, S, 7.73. Found: C, 52.24, H, 3.45, N, 6.64, S, 7.83.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 48 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 (860 mg) was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-d18d1bb7d458499c87dc64538d37a167
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613789B2

반응 노트

불러오는 중…