Dimethylformamide → (1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetonitrile
Reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([CH2:19]Cl)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[K+].[CH3:24][N:25](C)C=O>O>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([CH2:19][C:24]#[N:25])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 1-benzyl-4-chloromethyl-5-phenyl-1H-pyrazole (8.31 g), potassium cyanide (2.87 g), and N,N-dimethylformamide (100 ml) was stirred for 15 hours at 90° C., and poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and (1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetonitrile (3.50 g, yield: 44%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio).
Workup
- extractionwas extracted with ethyl acetate
- washThe ethyl acetate layer was washed with water
- dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e94eaae61c404a3094fc68d0602349e7
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179823B1
Reaction notes
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