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

HRID 2189938

Reaktionsgleichung

Reaktionsgleichung von HRID 2189938
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a638e7f0a56c46b29a46573153dbc2d2
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324257B2

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