Ammonium Hydroxide → 1-butyl-5-methyl-1H-pyrazole-3-carbonitrile

HRID 1360408Notes

Reaction equation

HRID 1360408 reaction equation
[CH2:1]([N:5]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]([NH2:13])=O)=[N:6]1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(Cl)=O.[OH-].[NH4+]>>[CH2:1]([N:5]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]#[N:13])=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 669589581-butyl-5-methyl-1H-pyrazole-3-carboxamide

Product 1

HCID 669586171-butyl-5-methyl-1H-pyrazole-3-carbonitrileYield 106.1%

Conditions

Temperature
90 °C

Procedure

A mixture of 1-butyl-5-methyl-1H-pyrazole-3-carboxamide (6.9 g, 38 mmol) and phosphorous oxychloride (34.0 mL) was heated at 90° C. under a nitrogen atmosphere for two hours and then allowed to cool to ambient temperature overnight. The reaction was poured into ice water (300 mL); concentrated ammonium hydroxide (115 mL) was added. The mixture was extracted with chloroform (3×), and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 6.58 g of 1-butyl-5-methyl-1H-pyrazole-3-carbonitrile as a pale yellow oil.

Workup

  1. temperatureto cool to ambient temperature overnight
  2. extractionThe mixture was extracted with chloroform (3×)
  3. dry with materialthe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f14302ca424440ab7af5f67257bf39b
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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