Nitric Acid → 1-Methyl-2,4,5-trinitroimidazole

HRID 968913Notes

Reaction equation

HRID 968913 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[N:4]=[C:3]1[N+:10]([O-:12])=[O:11].[N+:13]([O-])([OH:15])=[O:14].S(=O)(=O)(O)O>>[CH3:1][N:2]1[C:6]([N+:13]([O-:15])=[O:14])=[C:5]([N+:7]([O-:9])=[O:8])[N:4]=[C:3]1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 212761-Methyl-2,4-dinitro-1H-imidazole2×

Product 1

HCID 120301121-Methyl-2,4,5-trinitroimidazole

Procedure

Nitration of 1-methyl-2,4-dinitroimidazole with nitric acid and sulfuric acid Fuming nitric acid (4.0 ml, excess, d. 1.544 g/ml) was added to 1-methyl-2,4-dinitroimidazole (0.40 g, 2.33 mmol) at room temperature, following by sulfuric acid (2.0 ml, fuming 30% SO3) with stirring. The reaction temperature was then brought to 105° C. within 25 minutes and kept the temperature for further 2.0 hours. The reaction mixture was poured onto ice and the product was extracted with methylene chloride (3×20 ml). The combined organic phase was washed with water (15 ml), 10% aq. NaHCO3 (15 ml), and water (15 ml) and dried over Na2SO4. Evaporation of the solvent gave 1-methyl-2,4,5-trinitroimidazole as white solid, 110 mg (21%). 1H NMR (400 MHz, acetone-d6) δ 4.37. 13C NMR (100 MHz, acetone-d6) δ 139.9, 136.1, 133.4, 37.7.

Workup

  1. customfor further 2.0 hours
  2. additionThe reaction mixture was poured onto ice
  3. extractionthe product was extracted with methylene chloride (3×20 ml)
  4. washThe combined organic phase was washed with water (15 ml), 10% aq. NaHCO3 (15 ml), and water (15 ml)
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2cb2a87cac514733bca6d8d83cc4d6e1
Source dataset
uspto-grants-2007_12
Patent number
US07304164B1

Reaction notes

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