3-Benzoylpropionitrile → 3-(5-(2,5-Difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propanenitrile

HRID 2189938

반응식

HRID 2189938 반응식
O=[C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][C:5]#[N:6].[F:13][C:14]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:15]=1[C:16](=[S:19])[NH:17][NH2:18]>C(O)C>[F:13][C:14]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:15]=1[C:16]1[S:19][C:2]([CH2:3][CH2:4][C:5]#[N:6])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:18][N:17]=1

참가 물질

4

반응물 2

HCID 1384653-BenzoylpropionitrileHCID 55279024Benzenecarbothioic acid, 2,5-difluoro-, hydrazide

생성물 1

HCID 685529843-(5-(2,5-Difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propanenitrile수율 55%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

To a solution of 4-oxo-4-phenylbutanenitrile (0.076 g, 0.48 mmol) in ethanol (5 mL) was added 2,5-difluorobenzothiohydrazide (0.09 g, 0.48 mmol). After stirring at 90° C. for 16 hours, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed (20% ethyl acetate in hexanes) to provide the product (0.087 g, 55% yield).

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-a638e7f0a56c46b29a46573153dbc2d2
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324257B2

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