Water → 3-(5-nitro-2-furyl)-1H-pyrazole-4-carbonitrile

HRID 839218Notes

Reaction equation

HRID 839218 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([CH:14]=[N:15]O)=[CH:12][NH:11][N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O.O.C(=O)([O-])O.[Na+]>ClCCCl>[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14]#[N:15])=[CH:12][NH:11][N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178526569HCID 178526569, compound

Product 1

HCID 1785104403-(5-nitro-2-furyl)-1H-pyrazole-4-carbonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Heat Then g. of 3-(5-nitro-2-furyl)-1H-pyrazole-4-carboxaldehydeoxime together with 3.4 g of phosphorus oxychloride in 20 ml of 1,2-dichloroethane for 1 hour under reflux. To the resulting product add ice together with 50 ml of water. The adjust the pH to from 3 to 4 with sodium hydrogen carbonate and remove the formed crystals by vacuum filtration. Wash the crystals with water to obtain a 96% yield of 3-(5-nitro-2-furyl)-1H-pyrazole-4-carbonitrile [m.p. 237.5° to 239° C (from ethanol)].

Workup

  1. temperatureHeat
  2. customremove the formed crystals
  3. filtrationby vacuum filtration
  4. washWash the crystals with water

Sources & evidence

ORD record
ord-d0147a6b80da4f1aadf9c90ef54ae343
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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