Sulfuric Acid → 5-Amino-1-methyl-3-(1-methyl-5-nitro-2-imidazolyl)pyrazole-4-carboxamide

HRID 616619Notes

Reaction equation

HRID 616619 reaction equation
S(=O)(=O)(O)[OH:2].[NH2:6][C:7]1[N:11]([CH3:12])[N:10]=[C:9]([C:13]2[N:14]([CH3:21])[C:15]([N+:18]([O-:20])=[O:19])=[CH:16][N:17]=2)[C:8]=1[C:22]#[N:23]>C(O)C>[NH2:6][C:7]1[N:11]([CH3:12])[N:10]=[C:9]([C:13]2[N:14]([CH3:21])[C:15]([N+:18]([O-:20])=[O:19])=[CH:16][N:17]=2)[C:8]=1[C:22]([NH2:23])=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric Acid2×HCID 203681595-Amino-1-methyl-3-(1-methyl-5-nitro-2-imidazolyl)pyrazole-4-carbonitrile

Product 1

HCID 203681735-Amino-1-methyl-3-(1-methyl-5-nitro-2-imidazolyl)pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Another grouping present in these novel compounds, namely the 4-carbonitrile group, can also be utilized to prepare derivatives. This carbonitrile group can be readily hydrolyzed to the 4-carboxamido grouping by allowing the carbonitrile to react with concentrated sulfuric acid in absolute ethanol. Illustratively, when 5-amino-1-methyl-3-(1-methyl-5-nitro-2-imidazolyl)pyrazole-4-carbonitrile is allowed to react with concentrated sulfuric acid in absolute ethanol at steam bath temperature for about one hour, there is obtained 5-amino-1-methyl-3-(1-methyl-5-nitro-2-imidazolyl)-pyrazole-4-carboxamide.

Workup

  1. customto prepare derivatives

Sources & evidence

ORD record
ord-a3c2d1a2122e4cda9e6e168a45a81905
Source dataset
uspto-grants-1978_02
Patent number
US04075222

Reaction notes

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