2-Nitroimidazole → 1H-Imidazole, 1-(3-methyl-2-butenyl)-2-nitro-

HRID 968151Notes

Reaction equation

HRID 968151 reaction equation
C(=O)(O)[O-].[Na+].[CH3:6][C:7]([CH3:11])=[CH:8][CH2:9]Br.[N+:12]([C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)([O-:14])=[O:13]>C(#N)C>[CH3:6][C:7]([CH3:11])=[CH:8][CH2:9][N:16]1[CH:17]=[CH:18][N:19]=[C:15]1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 107012-NitroimidazoleHCID 700922-Butene, 1-bromo-3-methyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 113443651H-Imidazole, 1-(3-methyl-2-butenyl)-2-nitro-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium bicarbonate (0.42 g, 50 mmol) and dimethylallyl bromide (3.28 g, 22 mmol) were added to a suspension of 2-nitroimidazole (2.26 g, 20 mmol) in dry acetonitrile (10 mL). The mixture was stirred under reflux for 16 hours. The solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was filtered, and dried with anhydrous sodium sulfate. Removal of the solvent gave an oil which was recrystallized from petroleum ether (35-50° C.). Yield 1.83 g, m.p. 48-49° C. 1H NMR (CDCl3) δ 7.24 (s, 1H), 7.22 (s, 1H), 5.46 (m, 1H), 5.1 (d, 2H), 1.93 (s, 3H) and 1.90 (s, 3H).

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. filtrationThe solution was filtered
  5. dry with materialdried with anhydrous sodium sulfate
  6. customRemoval of the solvent
  7. customgave an oil which
  8. customwas recrystallized from petroleum ether (35-50° C.)

Sources & evidence

ORD record
ord-7fa1bb59e04f49e088304fb9ed8c8b6c
Source dataset
uspto-grants-2005_10
Patent number
US06958141B2

Reaction notes

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