Phosphorus oxychloride → HCID 19620693, compound

HRID 1984366Notes

Reaction equation

HRID 1984366 reaction equation
[CH2:1]([N:3]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([NH2:11])=O)=[N:4]1)[CH3:2].P(Cl)(Cl)(Cl)=O>>[CH2:1]([N:3]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]#[N:11])=[N:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66958306HCID 66958306, compound

Product 1

HCID 19620693HCID 19620693, compoundYield 90.6%

Procedure

1-Ethyl-5-methyl-1H-pyrazole-3-carboxamide (10.2 g, 66.7 mmol) was treated with phosphorus oxychloride (41 mL) according to the method described in Part C of Example 8. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 1-21% ethyl acetate/hexanes followed by 2-25% CMA in chloroform). The appropriate fractions were combined and concentrated under reduced pressure to yield 8.17 g of 1-ethyl-5-methyl-1H-pyrazole-3-carbonitrile as clear colorless crystals.

Workup

  1. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 1-21% ethyl acetate/hexanes followed by 2-25% CMA in chloroform)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b4ce09e81294194a4795456a0311bbb
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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