Sodium Cyanide → 2-(1-benzyl-5-phenyl-1H-pyrazol-3-yl)acetonitrile

HRID 1397459Notes

Reaction equation

HRID 1397459 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]([CH2:19]Br)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:21]#[N:22].[Na+].[OH-].[NH4+]>CN(C=O)C.O>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]([CH2:19][C:21]#[N:22])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8929Sodium Cyanide2×HCID 14923Ammonium HydroxideHCID 673248621-benzyl-3-(bromomethyl)-5-phenyl-1H-pyrazole

Product 1

HCID 673243062-(1-benzyl-5-phenyl-1H-pyrazol-3-yl)acetonitrileYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Benzyl-3-(bromomethyl)-5-phenyl-1H-pyrazole (200 mg, 0.6 mmol) and sodium cyanide (30 mg, 0.6 mmol) were stirred in DMF (6 mL). After several h, more sodium cyanide (60 mg, 1.2 mmol) was added to the reaction. A 25% ammonium hydroxide solution in water was added to the reaction and the reaction mixture was extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and concentrated under reduced pressure to yield 2-(1-benzyl-5-phenyl-1H-pyrazol-3-yl)acetonitrile (130 mg, yield 80%) MS (ESI) m/z: Calculated for C18H15N3: 273.13. found: 274.1 (M+H)+.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4d9fa84232a34dd78e227eb13fca303a
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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