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Imidazole → HCID 20735497, 화합물

HRID 353097
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HRID 353097 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:12][N:13]([CH2:17][CH2:18][OH:19])[C:14]=2[CH2:15][CH3:16])[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C=CN=C1.[C:30]([Si:34]([CH3:37])([CH3:36])Cl)([CH3:33])([CH3:32])[CH3:31]>CN(C)C=O>[Si:34]([O:19][CH2:18][CH2:17][N:13]1[C:14]([CH2:15][CH3:16])=[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:12]1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:37])[CH3:36]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10200330Ethyl 4-[(3,5-dichlorophenyl)sulfanyl]-5-ethyl-1-(2-hydroxyethyl)-1H-pyrazole-3-carboxylate

생성물 1

HCID 20735497HCID 20735497, 화합물수율 82.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of Example 46 (1.03 g, 2.65 mmol) in dimethylformamide (5 ml) was added imidazole (361 mg, 5.30 mmol), followed by tert-butyldimethylchlorosilane (600 mg, 3.97 mmol). The solution was stirred at room temperature for 4 days. The reaction mixture was partitioned between ethyl acetate and water and the aqueous phase was further extracted with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give a yellow oil. The crude product was purified by flash chromatography on silica gel eluting with cyclohexane:ethyl acetate (20:1, by volume), followed by cyclohexane:ethyl actetate (5:1, by volume) to afford the title compound (1.1 g) as a white powder, m.p. 83-84° C.

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionthe aqueous phase was further extracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a yellow oil
  7. customThe crude product was purified by flash chromatography on silica gel eluting with cyclohexane:ethyl acetate (20:1, by volume)

출처 및 근거

ORD 기록
ord-6a59298f72114cb38bc62f6569b45103
출처 데이터셋
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06750230B2

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