Ammonium Hydroxide → HCID 66958272, compound

HRID 1360413Notes

Reaction equation

HRID 1360413 reaction equation
[CH2:1]([N:8]1[C:12]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:11][C:10]([C:17]([NH2:19])=O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[OH-].[NH4+]>>[CH2:1]([N:8]1[C:12]([CH2:13][CH:14]([CH3:15])[CH3:16])=[CH:11][C:10]([C:17]#[N:19])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 66958785HCID 66958785, compound

Product 1

HCID 66958272HCID 66958272, compoundYield 99.8%

Conditions

Temperature
90 °C

Procedure

A mixture of 1-benzyl-5-(2-methylpropyl)-1H-pyrazole-3-carboxamide (6.77 g, 26.3 mmol) and phosphorous oxychloride (19 mL) was heated at 90° C. under a nitrogen atmosphere for 90 minutes and then allowed to cool to ambient temperature. The reaction was poured into ice water (250 mL); concentrated ammonium hydroxide (64 mL) was added. The mixture was extracted with tert-butyl methyl ether (3×150 mL), and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 6.28 g of 1-benzyl-5-(2-methylpropyl)-1H-pyrazole-3-carbonitrile as a pale orange oil.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe mixture was extracted with tert-butyl methyl ether (3×150 mL)
  3. dry with materialthe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cf1e9e07883f4ae5a7f8c06ab125dcf1
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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