Phosphorus oxychloride → 5-ethyl-1-methyl-1H-pyrazole-3-carbonitrile

Reaction equation

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

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 669585825-ethyl-1-methyl-1H-pyrazole-3-carboxamide

Product 1

HCID 669588435-ethyl-1-methyl-1H-pyrazole-3-carbonitrileYield 79.3%

Procedure

5-Ethyl-1-methyl-1H-pyrazole-3-carboxamide (3.8 g, 25 mmol) was treated with phosphorous oxychloride (18 mL, 0.19 mol) according to the method described in Part C of Example 8 to provide 2.68 g of 5-ethyl-1-methyl-1H-pyrazole-3-carbonitrile as a yellow oil.

Sources & evidence

ORD record: ord-2cfa7c89cd3d4cbab1825afbd52c9bf0
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145410B2

Reaction notes

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