Phosphorus oxychloride → HCID 66958933, compound

HRID 1360445Notes

Reaction equation

HRID 1360445 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]([NH2:16])=O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>>[CH2:1]([N:8]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]#[N:16])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66958295HCID 66958295, compound

Product 1

HCID 66958933HCID 66958933, compoundYield 13.1%

Conditions

Temperature
90 °C

Procedure

1-Benzyl-5-methyl-1H-pyrazole-3-carboxamide (28.22 g, 0.131 mol) was treated with phosphorus oxychloride (112 mL) according to the general method described in Part C of Example 8. The mixture was heated for 3 hours at 90° C. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 1-25% ethyl acetate in hexanes). The appropriate fractions were combined, dried over magnesium sulfate, and concentrated under reduced pressure to yield 3.38 g of 1-benzyl-5-methyl-1H-pyrazole-3-carbonitrile as a white solid.

Workup

  1. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 1-25% ethyl acetate in hexanes)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8c41385905e49efab44085e17d714e8
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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