2-((1,1-Dimethylethoxy)methyl)oxirane → 2-Tert-butoxymethyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

HRID 856160Notes

Reaction equation

HRID 856160 reaction equation
[N+]([C:4]1[NH:5][CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[N:8]=1)([O-])=O.[C:12]([O:16][CH2:17][CH:18]1[CH2:20][O:19]1)([CH3:15])([CH3:14])[CH3:13].C([O-])(=O)C.[Na+]>C(O)C>[C:12]([O:16][CH2:17][CH:18]1[O:19][C:4]2=[N:8][C:7]([N+:9]([O-:11])=[O:10])=[CH:6][N:5]2[CH2:20]1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 243142-((1,1-Dimethylethoxy)methyl)oxiraneHCID 517045Sodium AcetateHCID 178526857HCID 178526857, compound

Product 1

HCID 230814422-Tert-butoxymethyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazoleYield 21%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-Dinitro-1H-imidazole (10 g, 63.3 mmol), 2-tert-butoxymethyloxirane (27 ml, 189 mmol) and sodium acetate (5.19 g, 189 mmol) were suspended in ethanol (100 ml) followed by stirring under reflux for 17 hours. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. Water was added to the residue, and the resulting mixture was extracted with methylene chloride. The organic phase was dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1) to afford 2-tert-butoxymethyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (3.2 g, yield 21%) as a white powder.

Workup

  1. temperatureunder reflux for 17 hours
  2. customto return to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe resulting mixture was extracted with methylene chloride
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1)

Sources & evidence

ORD record
ord-f44074ed7f6f48648ffe1aa4e33f7f13
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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