3-Bromo-1,1,1-trifluoro-2-propanone → 2-[4-Hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1h-imidazol-2-yl]thiophene

HRID 1166377노트

반응식

HRID 1166377 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[NH:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)(O)[O-].[Na+].Br[CH2:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28]>C(O)(C)C>[OH:31][C:26]1([C:27]([F:30])([F:29])[F:28])[CH2:25][N:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[C:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[N:13]1

참가 물질

5

반응물 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178504800HCID 178504800, 화합물

생성물 1

HCID 229979092-[4-Hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1h-imidazol-2-yl]thiophene수율 39.7%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
82.5 °C

실험 절차

To a mixture of the amidine of step 1 (2.0 g, 7.1 mmol) and sodium bicarbonate (1.2 g, 14.3 mmol) in isopropanol (200 ml), 3-bromo-1,1, 1-trifluoroacetone 1.1 ml, 10.7 mmol) was added. After heating at 80-85° C. for 16 hours, the reaction mixture was cooled and filtered. The residue was washed with methylene chloride and the combined organic fractions were dried over sodium sulfate, filtered and concentrated. The crude mixture (25.7 g) was purified by chromatography (silica gel, ethyl acetate/hexane 55/45) to give the 4,5-dihydro-imidazole (1.1 g, 38%) as a white solid: mp (DSC) 214° C. Anal. Calc'd. for C15H13N2S2O3F3: C, 46.15, H, 3.36, N, 7.18, S, 16.43. Found: C, 46.09, H, 3.26, N, 7.07, S, 16.71.

후처리

  1. additionwas added
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. washThe residue was washed with methylene chloride
  5. dry with materialthe combined organic fractions were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude mixture (25.7 g) was purified by chromatography (silica gel, ethyl acetate/hexane 55/45)

출처 및 근거

ORD 기록
ord-d3f9a7c11ac24dd6934b49b84789c5d6
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613789B2

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