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

HRID 839247Notes

Reaction equation

HRID 839247 reaction equation
Cl.N[C:3]1[C:4]([C:14]2[O:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)=[N:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.N([O-])=O.[Na+].[N:26]1C=CC=C[CH:27]=1>S(=O)(=O)(O)O.O>[N+:19]([C:16]1[O:15][C:14]([C:4]2[C:3]([C:27]#[N:26])=[CH:7][N:6]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:5]=2)=[CH:18][CH:17]=1)([O-:21])=[O:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 20326032HCID 20326032, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 203261583-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
90 °C

Procedure

Add a solution of 0.25 g of 4-amino-3-(5-nitro-2-furyl)-1-phenylpyrazole hydrochloride in 2 ml of pyridine dropwise over a period of from 1 to 2 hours to a solution of 0.22 g of sodium nitrite in 3 ml of concentrated sulfuric acid and 1.75 ml of water at 0° C. Stir the resulting reaction mixture for 0.5 hour, and then precipitate the diazonium salt by adding ice and water to the reaction mixture. Add the precipitate to a heated (90° C) solution of 300 mg of potassium cyanide and 200 ml of copper(I)cyanide in 20 ml of water. Stir the prepared admixture for 15 minutes at 90° C, cool down, draw off the formed precipitate and chromatograph with methylene chloride on silica gel to obtain 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carbonitrile [m.p. 190° to 192° C].

Workup

  1. customthe resulting reaction mixture for 0.5 hour
  2. customprecipitate the diazonium salt
  3. additionby adding ice and water to the reaction mixture
  4. additionAdd the precipitate to
  5. stirringStir the prepared admixture for 15 minutes at 90° C
  6. temperaturecool down

Sources & evidence

ORD record
ord-62b8ad717e6b4ab58d36c08678c6ca80
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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