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

HRID 2189938

Reaction equation

HRID 2189938 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a638e7f0a56c46b29a46573153dbc2d2
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Linked notes

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