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Dimethylformamide dimethyl acetal → HCID 67258869, 화합물

HRID 2359021
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HRID 2359021 반응식
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:15])[CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>CN(C)C=O>[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:15])[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:18][N:19]([CH3:21])[CH3:20])=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 78373Dimethylformamide dimethyl acetalHCID 65583291HCID 65583291, 화합물

생성물 1

HCID 67258869HCID 67258869, 화합물수율 53.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 1-(5-chloro-2-thienyl)-2-(pyridin-4-yl)ethanone (21 mmol) in 13 mL N,N-dimethylformamide, was added N,N-dimethylformamide dimethyl acetal (71.5 mmol). The mixture was refluxed for 3 h and then allowed to cool to room temperature. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried over MgSO4 filtered and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol 100:1 to 20:1) to afford 3.3 g (51% yield) of 1-(5-chloro-2-thienyl)-3-(dimethylamino)-2-(pyridin-4-yl)prop-2-en-1-one.

후처리

  1. temperatureThe mixture was refluxed for 3 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol 100:1 to 20:1)

출처 및 근거

ORD 기록
ord-91a0bc7bc719400ea9ff771dc2785820
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08685974B2

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