2-Propynenitrile → 3,3-bis(trifluoromethyl)-5-cyano-3H-pyrazole

HRID 917891Notes

Reaction equation

HRID 917891 reaction equation
[F:1][C:2]([C:5]([C:8]([F:11])([F:10])[F:9])=[N+:6]=[N-:7])([F:4])[F:3].[C:12]([C:14]#[CH:15])#[N:13]>>[F:1][C:2]([F:4])([F:3])[C:5]1([C:8]([F:9])([F:10])[F:11])[CH:15]=[C:14]([C:12]#[N:13])[N:7]=[N:6]1

Participants

3

Reactant 2

HCID 140552-PropynenitrileHCID 125761642-Diazo-1,1,1,3,3,3-hexafluoropropane

Product 1

HCID 215241473,3-bis(trifluoromethyl)-5-cyano-3H-pyrazoleYield 87.6%

Conditions

Temperature
50 °C

Procedure

A sealed glass tube containing 36.2 g of bis(trifluoromethyl)diazomethane and 10.2 g of cyanoacetylene was heated at 50°C for 24 hours. The product was distilled to give 40.1 g of 3,3-bis(trifluoromethyl)-5-cyano-3H-pyrazole, bp 38°C/12 mm. The ultraviolet, infrared, and mass spectra as well as the proton and fluorine nuclear magnetic resonance spectra were consistent with the proposed structure.

Workup

  1. distillationThe product was distilled

Sources & evidence

ORD record
ord-035d16fc6c3c47899705387996336489
Source dataset
uspto-grants-1976_07
Patent number
US03968137

Reaction notes

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