1-Methyl-2,4-dinitro-1H-imidazole → 1-Methyl-2,4,5-trinitroimidazole

HRID 968914Notes

Reaction equation

HRID 968914 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[CH3:9][N:10]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[N:12]=[C:11]1[N+:18]([O-:20])=[O:19]>C(Cl)Cl>[CH3:9][N:10]1[C:14]([N+:7]([O-:8])=[O:6])=[C:13]([N+:15]([O-:17])=[O:16])[N:12]=[C:11]1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 212761-Methyl-2,4-dinitro-1H-imidazoleHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 120301121-Methyl-2,4,5-trinitroimidazoleYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Nitronium tetrafluoroborate (NO2BF4, 5.0 g, 37.6 mmol) was added to the solid of 1-methyl-2,4-dinitroimidazole (4.0 g, 23.3 mmol) at room temperature. Then the reaction temperature was brought to 105° C. within 15 minutes. At that temperature, all solids melted. The reaction mixture was then stirred at that temperature for 1.5 hrs, then cooled to room temperature and diluted with methylene chloride before being poured onto ice/water. The product was extracted with methylene chloride (3×60 ml). The combined organic phase was washed successively with water (50 ml), 10% aq. NaHCO3 (30 ml), and water (50 ml) and dried over Na2SO4. The solvent was removed in vacuo and the residue was recrystallized with ethanol to give 3.72 g (74%) of 1-methyl-2,4,5-trinitroimidazole as pale yellow crystals, mp=84.0-85.0° C. (literature, mp=82° C.). The structure of the compound was confirmed by NMR spectroscopy.

Workup

  1. additionbefore being poured onto ice/water
  2. extractionThe product was extracted with methylene chloride (3×60 ml)
  3. washThe combined organic phase was washed successively with water (50 ml), 10% aq. NaHCO3 (30 ml), and water (50 ml)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was recrystallized with ethanol

Sources & evidence

ORD record
ord-7a42116c8670469f8c5a3d78bfdf8f7b
Source dataset
uspto-grants-2007_12
Patent number
US07304164B1

Reaction notes

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