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

HRID 839221Notes

Reaction equation

HRID 839221 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[O:12][C:11]([C:13]2[C:17]([CH:18]=[N:19]O)=[CH:16][N:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:14]=2)=[CH:10][CH:9]=1)([O-:7])=[O:6]>C(Cl)(Cl)(Cl)Cl>[N+:5]([C:8]1[O:12][C:11]([C:13]2[C:17]([C:18]#[N:19])=[CH:16][N:15]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:14]=2)=[CH:10][CH:9]=1)([O-:7])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54343732N-{[3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]methylidene}hydroxylamine

Product 1

HCID 203261583-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Add 9.4 ml of thionyl chloride to a suspension of 32.6 g of finely-ground 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehydeoxime in 250 ml of carbon tetrachloride at 60° to 65° C. Stir the resulting admixture for 1.5 hours at this temperature and for 2 hours under reflux. Separate the formed precipitate by vacuum filtration at room temperature. Wash the filter residue (precipitate) with carbon tetrachloride and dry to obtain a 96% yield of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carbonitrile [m.p. 190° to 192° C].

Workup

  1. temperaturefor 2 hours under reflux
  2. customSeparate the formed precipitate
  3. filtrationby vacuum filtration at room temperature
  4. washWash the filter residue (precipitate) with carbon tetrachloride
  5. customdry

Sources & evidence

ORD record
ord-eba5221b161847498296e3619d6831c0
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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