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

HRID 1642768Notes

Reaction equation

HRID 1642768 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].[N+:9]([O-])([OH:11])=[O:10]>C(O)(=O)C>[N+:9]([N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[CH:6]1)([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178526856HCID 178526856, compound

Product 1

HCID 51694961,4-Dinitro-1H-imidazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

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, the resultant was poured into 3 kg of ice cubes to obtain 1,4-dinitroimidazole as white precipitates. Then the precipitates, still cool, were immediately filtered out, washed with cold water so as to remove the residual acid, and then dried, resulting in 178.6 g(68% yield) of 1,4-dinitroimidazole in a fine white powder form. The structure of the resulted 1,4-dinitroimidazole was determined by NMR analysis, 1H-NMR and 13C-NMR. The results are shown below:

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

Sources & evidence

ORD record
ord-949fe7ee40574d81b6f4c65cde82768f
Source dataset
uspto-grants-2012_02
Patent number
US08119679B2

Reaction notes

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