Pyrazole → 4-(1-Pyrazolyl)benzonitrile

HRID 625416Notes

Reaction equation

HRID 625416 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[OH-].[Na+].CN(C)C=O.F[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1>O>[N:1]1([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 6228DimethylformamideHCID 145174-FluorobenzonitrileHCID 14798Sodium Hydroxide

Product 1

HCID 120796294-(1-Pyrazolyl)benzonitrileYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 1H-pyrazole (422 mg, 6.21 mmol, 1.50 equiv), sodium hydroxide (248 mg, 6.20 mmol, 1.50 equiv), and N,N-dimethylformamide (20 mL). The mixture was stirred and heated to 80° C. for 30 min, then to this was added 4-fluorobenzonitrile (500 mg, 4.13 mmol, 1.00 equiv). The resulting solution was stirred for 3 h at 110° C. in an oil bath. The resulting solution was diluted with 50 mL of H2O. The solids were collected by filtration and dried in an oven. The product was obtained as 0.43 g (62%) of a white solid.

Workup

  1. customInto a 50-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred for 3 h at 110° C. in an oil bath
  4. filtrationThe solids were collected by filtration
  5. customdried in an oven

Sources & evidence

ORD record
ord-cf7ffd78fa744d07975375ee6b3aebe4
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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