Sulfuric Acid → 1-Methyl-4-nitro-1H-imidazole-2-carbaldehyde

HRID 224504Notes

Reaction equation

HRID 224504 reaction equation
Cl[CH:2](Cl)[C:3]1[N:4]([CH3:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[N:7]=1.S(=O)(=O)(O)[OH:14].[OH-].[Na+]>>[CH:2]([C:3]1[N:4]([CH3:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[N:7]=1)=[O:14]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 23462459HCID 23462459, compound

Product 1

HCID 141113101-Methyl-4-nitro-1H-imidazole-2-carbaldehydeYield 83%

Procedure

21 parts of 2-dichloromethyl-1-methyl-4-nitroimidazole in 80 parts by volume of 10 percent strength by weight sulfuric acid are stirred for 2 hours at 100° C. The solution is cooled, poured onto ice and neutralized with 55 parts of 6N sodium hydroxide solution. The aqueous phase is extracted with 4 times 50 parts by volume of methylene chloride. The combined extracts are dried (? and evaporated). 13 parts of 2-formyl-1-methyl-4nitroimidazole (83% of theory) of melting point 129° C. are obtained.

Workup

  1. temperatureThe solution is cooled
  2. extractionThe aqueous phase is extracted with 4 times 50 parts by volume of methylene chloride
  3. customThe combined extracts are dried
  4. custom(? and evaporated)

Sources & evidence

ORD record
ord-c13b9a1c0bab4859baf23d74793ae61a
Source dataset
uspto-grants-1980_11
Patent number
US04232165

Reaction notes

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