Sulfuric Acid → 1-Methyl-5-nitro-1H-imidazole-2-carbaldehyde

HRID 224503Notes

Reaction equation

HRID 224503 reaction equation
Cl[CH:2](Cl)[C:3]1[N:4]([CH3:11])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][N:7]=1.S(=O)(=O)(O)[OH:14].[OH-].[Na+]>>[CH:2]([C:3]1[N:4]([CH3:11])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][N:7]=1)=[O:14]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 15372234HCID 15372234, compound

Product 1

HCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehyde

Procedure

210 parts of 2-dichloromethyl-1-methyl-5-nitroimidazole are stirred in 800 parts by volume of 10 percent strength by weight sulfuric acid for 2 hours at 100° C. The mixture is then neutralized with 550 parts of 6N sodium hydroxide solution, with intense cooling, and the resulting solution is extracted with 4 times 500 parts by volume of methylene chloride. The combined extracts are dried. 126 parts (82% of theory) of 2-formyl-1-methyl-5-nitroimidazole of melting point 93° C. (after recrystallization from toluene) are obtained.

Workup

  1. extractionthe resulting solution is extracted with 4 times 500 parts by volume of methylene chloride
  2. customThe combined extracts are dried
  3. custom126 parts (82% of theory) of 2-formyl-1-methyl-5-nitroimidazole of melting point 93° C. (after recrystallization from toluene)
  4. customare obtained

Sources & evidence

ORD record
ord-6ab8effb28d34ee7891a4b42384f1561
Source dataset
uspto-grants-1980_11
Patent number
US04232165

Reaction notes

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