Sodium hydride → HCID 23081200, compound

HRID 856234Notes

Reaction equation

HRID 856234 reaction equation
Cl[C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:10][C:11]1([CH2:14][N:15]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[C:18](=[O:25])[O:17][C:16]2=O)[CH2:13][O:12]1.[C:27]([O-])(=O)C.[Na+].[H-].[Na+]>C(O)C>[CH2:16]([O:17][C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:15][CH2:14][C:11]1([CH3:13])[O:12][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1)=[O:25])[CH3:27]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 517045Sodium AcetateHCID 86604806HCID 86604806, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 23081200HCID 23081200, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-4-nitro-1H-imidazole (891 mg, 6.04 mmol), 1-(2-methyloxiran-2-ylmethyl)-1H-benzo[d][1,3]oxazin-2,4-dione (1.41 g, 6.04 mmol), sodium acetate (545 mg, 6.64 mmol) and ethanol (10 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, water was added, and the solution was extracted with methylene chloride. The organic phase was washed with a saturated saline solution and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was dissolved in 1,4-dioxane (20 ml). To the solution, sodium hydride (219 mg, 5.48 mmol) was added followed by stirring under reflux for 5 hours. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, ice-water was added, and the precipitates were filtered off, which were purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1) to afford N-(2-ethoxycarbonylphenyl)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethylamine (1.15 g, yield 55%) 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, water was added
  5. extractionthe solution was extracted with methylene chloride
  6. washThe organic phase was washed with a saturated saline solution
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. dissolutionthe residue was dissolved in 1,4-dioxane (20 ml)
  11. stirringby stirring
  12. temperatureunder reflux for 5 hours
  13. customto return to room temperature
  14. concentrationconcentrated under reduced pressure
  15. additionTo the residue, ice-water was added
  16. filtrationthe precipitates were filtered off
  17. customwhich were purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-5f0e3997d86f41e2bb66768e8632a1e9
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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