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

HRID 2286735Notes

Reaction equation

HRID 2286735 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 6 N 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-4-nitroimidazole (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. customevaporated

Sources & evidence

ORD record
ord-d130bfe3a55c483c8f1dd554d79e00e3
Source dataset
uspto-grants-1981_05
Patent number
US04267349

Reaction notes

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