Ethanol → 3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carboxamide

HRID 839227

Reaction equation

HRID 839227 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14]#[N:15])=[CH:12][N:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(=O)(=O)(O)[OH:23].C(O)C>O>[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14]([NH2:15])=[O:23])=[CH:12][N:11]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 203261583-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonitrile

Product 1

HCID 203261233-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carboxamideYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 10 g of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carbonitrile to a mixture of 20 ml of concentrated sulfuric acid and 20 ml of ethanol. Heat the resulting reaction mixture for 1.5 hours in a water bath at 90° to 100° C. Pour the solution onto ice and water to obtain a 93% yield of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxamide [m.p. 236° to 238° C (from dimethylformamide/methanol)].

Workup

  1. temperatureHeat
  2. customthe resulting reaction mixture for 1.5 hours in a water bath at 90° to 100° C

Sources & evidence

ORD record
ord-51cc8317fae14eab93da2a3970900588
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Linked notes

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