Sulfuric Acid → 1-Methyl-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carboxamide

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]#[N:8])[C:4]([C:9]2[O:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)=[N:3]1.S(=O)(=O)(O)[OH:18]>>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([NH2:8])=[O:18])[C:4]([C:9]2[O:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)=[N:3]1

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 203260431-Methyl-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 203260601-Methyl-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carboxamideYield 97%

Procedure

While cooling and stirring 80 ml of concentrated sulfuric acid at room temperature, add 40 g of 1-methyl-3-(5-nitro-2-furyl)pyrazole-4-carbonitrile thereto. Then stir the resulting mixture for 21 hours at room temperature. Pour thus-obtained solution onto ice for a 97% yield of 1-methyl-3-(5-nitro-2-furyl)pyrazole-4-carboxamide [m.p. 251° to 252.5° C].

Workup

temperatureWhile cooling
additionPour

Sources & evidence

ORD record: ord-44ad9a5e28a44eef93c5a6469008066a
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04093812

Reaction notes

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