Sodium hydride → HCID 23081267, compound

HRID 856356Notes

Reaction equation

HRID 856356 reaction equation
Cl[C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[Br:10][C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17](=[O:19])[N:16]([CH2:20][C:21]3([CH3:24])[CH2:23][O:22]3)[C:15]=2[CH:25]=1.C([O-])(=O)C.[Na+].[H-].[Na+]>C(O)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17](=[O:19])[N:16]([CH2:20][C:21]3([CH3:23])[O:22][C:2]4=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]4[CH2:24]3)[C:15]=2[CH:25]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 517045Sodium AcetateHCID 23081533HCID 23081533, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 23081267HCID 23081267, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2-chloro-4-nitro-1H-imidazole (3.22 g, 21.8 mmol), 5-bromo-3-(2-methyloxiran-2-ylmethyl)-3H-benzoxazol-2-one (6.2 g, 21.8 mmol); sodium acetate (1.97 g, 24 mmol) and ethanol (50 ml) was stirred under reflux for 8 hours. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, water was added, and the resulting 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 dissolved in 1,4-dioxane (60 ml). To the solution, sodium hydride (528 mg, 13.21 mmol) was added followed by stirring at 70-80° C. for 17 hours. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, water was added, 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=30/1) to afford 5-bromo-3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)-3H-benzoxazol-2-one (1.82 g, yield 37%) as a white powder.

Workup

  1. temperatureunder reflux for 8 hours
  2. customto return to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue, water was added
  5. extractionthe resulting solution was extracted with methylene chloride
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. dissolutionthe residue was dissolved in 1,4-dioxane (60 ml)
  10. customto return to room temperature
  11. concentrationconcentrated under reduced pressure
  12. additionTo the residue, water was added
  13. extractionextracted with methylene chloride
  14. dry with materialThe organic phase was dried over magnesium sulfate
  15. filtrationfiltered
  16. concentrationThe filtrate was concentrated under reduced pressure
  17. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=30/1)

Sources & evidence

ORD record
ord-10eb5c6a2409493f823db5318aee0494
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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