Acetic Acid → 1,4-Dinitro-1H-imidazole

HRID 1642769Notes

Reaction equation

HRID 1642769 reaction equation
C(O)(=O)C.[N+:5]([C:8]1[N:9]=[CH:10][NH:11][CH:12]=1)([O-:7])=[O:6].[N+:13]([O-])([OH:15])=[O:14]>O>[N+:13]([N:11]1[CH:12]=[C:8]([N+:5]([O-:7])=[O:6])[N:9]=[CH:10]1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 944Nitric AcidHCID 178526856HCID 178526856, compound

Product 1

HCID 51694961,4-Dinitro-1H-imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

430 mL of acetic acid and 188 g of 4-nitroimidazole were charged into a 2 L-volume reactor and stirred. While stirring the mixture, 100% nitric acid(137 mL) was slowly added dropwise to the mixture at the reaction temperature of 35° C. Anhydrous acetic acid(318 mL) was added dropwise thereto at 25° C. over 1 hour. After stirring the reaction mixture at 25° C. for 2 days, 1,4-dinitroimidazole was synthesized. Then, the resultant was poured in 2 L cold water, and extracted three times with 500 mL of methyl chloride for each time. The obtained methylene chloride solution was dried over MgSO4 so as to completely remove the water therefrom, resulting in methylene chloride extract solution containing 1,4-dinitroimidazole. The structure of the obtained 1,4-dinitroimidazole was as same as that of the comparative example.

Workup

  1. additionwas slowly added dropwise to the mixture at the reaction temperature of 35° C
  2. stirringAfter stirring the reaction mixture at 25° C. for 2 days
  3. extractionextracted three times with 500 mL of methyl chloride for each time
  4. dry with materialThe obtained methylene chloride solution was dried over MgSO4 so as
  5. customto completely remove the water
  6. customresulting in methylene chloride
  7. extractionextract solution
  8. additioncontaining 1,4-dinitroimidazole

Sources & evidence

ORD record
ord-237c03f6665b44e9b6d3d3986fb5e074
Source dataset
uspto-grants-2012_02
Patent number
US08119679B2

Reaction notes

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