Sodium hydride → HCID 23081223, compound

HRID 856363Notes

Reaction equation

HRID 856363 reaction equation
[CH3:1][C:2]1([CH2:5][N:6]2[CH2:10][CH2:9][O:8][C:7]2=[O:11])[CH2:4][O:3]1.Cl[C:13]1[NH:14][CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[N:17]=1.C([O-])(=O)C.[Na+].[H-].[Na+]>C(O)C>[CH3:1][C:2]1([CH2:5][N:6]2[CH2:10][CH2:9][O:8][C:7]2=[O:11])[O:3][C:13]2=[N:17][C:16]([N+:18]([O-:20])=[O:19])=[CH:15][N:14]2[CH2:4]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 517045Sodium AcetateHCID 23081569HCID 23081569, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 23081223HCID 23081223, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(2-methyloxiran-2-ylmethyl)-oxazolidin-2-one (2.87 g, 18.23 mmol), 2-chloro-4-nitro-1H-imidazole (2.7 g, 18.23 mmol), sodium acetate (1.64 g, 20.05 mmol) and ethanol (30 ml) was stirred under reflux for 10 hours. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, methylene chloride was added, and the resulting solution was washed with water, a saturated sodium hydrogencarbonate solution and a saturated saline solution in this order, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was dissolved in 1,4-dioxane (50 ml). To the solution, sodium hydride (610 mg, 15.25 mmol) was added followed by stirring under reflux overnight. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, water was added, and the solution was extracted with methylene chloride. The organic phase was dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1) to afford 3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)oxazolidin-2-one (1.54 g, yield 40%) as a white powder.

Workup

  1. temperatureunder reflux for 10 hours
  2. customto return to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue, methylene chloride was added
  5. washthe resulting solution was washed with water
  6. dry with materiala saturated sodium hydrogencarbonate solution and a saturated saline solution in this order, dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. dissolutionthe residue was dissolved in 1,4-dioxane (50 ml)
  10. stirringby stirring
  11. temperatureunder reflux overnight
  12. customto return to room temperature
  13. concentrationconcentrated under reduced pressure
  14. additionTo the residue, water was added
  15. extractionthe solution was extracted with methylene chloride
  16. dry with materialThe organic phase was dried over magnesium sulfate
  17. filtrationfiltered
  18. concentrationThe filtrate was concentrated under reduced pressure
  19. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-6114daa6b914407d88a5aae3930f86a8
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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