Water → 4-(1-Pyrazolyl)benzonitrile

HRID 1259318Notes

Reaction equation

HRID 1259318 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH:14]=[CH:13][CH:12]=[N:11]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[N:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 120796294-(1-Pyrazolyl)benzonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

4-Fluorobenzonitrile (204.2 g), pyrazole (138.6 g, 1.22 eq) and potassium carbonate (281.5 g, 1.22 eq) in DMF (1110 ml) were heated at 120° C. for 7 hours. The suspension was cooled to 25° C. and water (2920 ml) added. The reaction was extracted with MTBE (3×1460 ml) and the combined extracts were washed with water (3×1460 ml) and saturated aqueous sodium chloride (1460 ml). The organic phase was concentrated at atmospheric pressure until the pot temperature rose to 65° C. Heptane (1700 ml) was added over 30 minutes at 60-65° C., and then a further 300 ml of distillate was collected. The solution was stirred at 60-65° C. for 15 minutes and then cooled to <5° C. The slurry was filtered and washed with heptane (2×200 ml), and dried under vacuum to constant weight to give the title compound as a solid (245.3 g, 87%).

Workup

  1. extractionThe reaction was extracted with MTBE (3×1460 ml)
  2. washthe combined extracts were washed with water (3×1460 ml) and saturated aqueous sodium chloride (1460 ml)
  3. concentrationThe organic phase was concentrated at atmospheric pressure until the pot temperature
  4. customrose to 65° C
  5. additionHeptane (1700 ml) was added over 30 minutes at 60-65° C.
  6. distillationa further 300 ml of distillate was collected
  7. temperaturecooled to <5° C
  8. filtrationThe slurry was filtered
  9. washwashed with heptane (2×200 ml)
  10. customdried under vacuum to constant weight

Sources & evidence

ORD record
ord-f3646d6af89c48f69ce8da0f827321e2
Source dataset
uspto-grants-2013_06
Patent number
US08466284B2

Reaction notes

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