3-Bromo-1,1,1-trifluoro-2-propanone → 4-hydroxy-1-[4-(methylsulfonyl)phenyl]-2-phenyl-4-trifluoromethyl-4,5-dihydro-1H-imidazole

HRID 52326

반응식

HRID 52326 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[NH:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)(O)[O-].[Na+].Br[CH2:26][C:27](=[O:32])[C:28]([F:31])([F:30])[F:29]>C(O)(C)C>[OH:32][C:27]1([C:28]([F:31])([F:30])[F:29])[CH2:26][N:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=2)[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:13]1

참가 물질

5

반응물 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178504794HCID 178504794, 화합물

생성물 1

HCID 107625654-hydroxy-1-[4-(methylsulfonyl)phenyl]-2-phenyl-4-trifluoromethyl-4,5-dihydro-1H-imidazole

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a mixture of N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (Step 1) (10 mmol) and sodium bicarbonate (20 mmol) in isopropanol (100 mL), 3-bromo-1,1,1-trifluoroacetone (20 mmol) is added. After heating the reaction mixture at 70°-75° C. for 20 hours, the solvent is removed. The residue is redissolved in methylene chloride and washed with water. The organic fractions are combined, dried over sodium sulfate, filtered and concentrated in vacuo. The crude mixture is chromatographed (silica gel, toluene/ethyl acetate, 7/3) to give 4-hydroxy-1-[4-(methylsulfonyl)phenyl]-2-phenyl -4-trifluoromethyl-4,5-dihydro-1H-imidazole.

후처리

  1. additionis added
  2. temperatureAfter heating the reaction mixture at 70°-75° C. for 20 hours
  3. customthe solvent is removed
  4. dissolutionThe residue is redissolved in methylene chloride
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude mixture is chromatographed (silica gel, toluene/ethyl acetate, 7/3)

출처 및 근거

ORD 기록
ord-b4007b73d2ec4668b552bfcb37a73e05
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616601

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