Thionyl Chloride → 3-(5-Nitrofuran-2-yl)-1-(propan-2-yl)-1H-pyrazole-4-carbonitrile

HRID 839220Notes

Reaction equation

HRID 839220 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([CH:9]=[N:10]O)[C:6]([C:12]2[O:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[N:5]1)([CH3:3])[CH3:2].S(Cl)(Cl)=O>ClCCCl>[CH:1]([N:4]1[CH:8]=[C:7]([C:9]#[N:10])[C:6]([C:12]2[O:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[N:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54174528HCID 54174528, compound

Product 1

HCID 203262393-(5-Nitrofuran-2-yl)-1-(propan-2-yl)-1H-pyrazole-4-carbonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Stir an admixture of 3.4 g of finely pulverized 1-isopropyl-3-(5-nitro-2-furyl)pyrazole-4-carboxaldehydeoxime in 15 ml of 1,2-dichloroethane with 1.8 g of thionyl chloride for 80 minutes at 55° C. Evaporate the resulting solution to dryness in vacuo and then evaporate to dryness twice more after mixing with 1,2-dichloroethane to obtain a 99% yield of 1-isopropyl-3-(5-nitro-2-furyl)pyrazole-4-carbonitrile [m.p. 181° to 182° C (from ethanol)].

Workup

  1. customEvaporate the resulting solution to dryness in vacuo
  2. customevaporate to dryness twice more
  3. additionafter mixing with 1,2-dichloroethane

Sources & evidence

ORD record
ord-971fce8fe12045ab826c3779d49a4bde
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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