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

HRID 273650Notes

Reaction equation

HRID 273650 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.C(OC(=O)C)(=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

5

Reactant 2

HCID 944Nitric AcidHCID 178526856HCID 178526856, compound

Product 1

HCID 51694961,4-Dinitro-1H-imidazole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

4-nitroimidazole (88 gms.) obtained from Fluka Chemical Company, Ronkonkoma, N.Y, was dissolved in glacial acetic acid (240 ml ) and acetic anhydride (120 ml). Nitric acid (98%, 80 ml. density=1.52 gm/cc) was added dropwise while continuously stirring the mixture over a period of 60 min. The mixture is then stirred at room temperature for another 3 hrs.. The mixture gradually turned into a golden yellow color solution. This solution was poured onto crushed ice, stirred for about 1 hour and filtered the precipitate. The sample was dried completely, and 85 grms. of 1,4 -dinitroimidazole was recovered having a melting point of 92° C. corresponding to the reported melting point in the literature. The structure was further confirmed by NMR (1H NMR, in CDCl3, 9.0 and 9.4 ) and Mass (M+ 158) Spectroscopy techniques.

Workup

  1. stirringThe mixture is then stirred at room temperature for another 3 hrs
  2. additionThis solution was poured
  3. customonto crushed ice
  4. stirringstirred for about 1 hour
  5. filtrationfiltered the precipitate
  6. customThe sample was dried completely
  7. customof 1,4 -dinitroimidazole was recovered

Sources & evidence

ORD record
ord-4daa4cf2299b4a52bd61b9463feb871b
Source dataset
uspto-grants-1995_02
Patent number
US05387297

Reaction notes

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