Sodium hydride → HCID 23081337, compound

HRID 856348Notes

Reaction equation

HRID 856348 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[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:17][C:16]2=[O:26])[CH2:13][O:12]1.C(=O)([O-])O.[Na+].[H-].[Na+]>O.C(O)C>[CH3:13][C:11]1([CH2:14][N:15]2[N:19]=[C:18]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:17][C:16]2=[O:26])[O:12][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 23081544HCID 23081544, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 23081337HCID 23081337, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 2-chloro-4-nitro-1H-imidazole (170 mg, 1.15 mmol), 3-(2-methyloxiran-2-ylmethyl)-5-phenyl-3H-[1,3,4]oxadiazol-2-one (310 mg, 0.9 mmol), sodium hydrogencarbonate (120 mg, 1.43 mmol) and ethanol (2 ml) was stirred under reflux for 2.5 hours. The reaction mixture was allowed to return to room temperature, then diluted with water. 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, the residue was dissolved in 1,4-dioxane (10 ml). To the solution, sodium hydride (55 mg, 1.38 mmol) was added followed by stirring at room temperature for 1 hour and then stirring under reflux for 1.5 hours. The reaction mixture was allowed to return to room temperature. To the solution, water was added, and the mixture 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 recrystallized from ethanol to afford 3-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-5-phenyl-3H-[1,3,4]-oxadiazol-2-one (127 mg, yield 32%) as a light brown powder.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. customto return to room temperature
  3. extractionThe solution was extracted with methylene chloride
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in 1,4-dioxane (10 ml)
  8. stirringby stirring at room temperature for 1 hour
  9. stirringstirring
  10. temperatureunder reflux for 1.5 hours
  11. customto return to room temperature
  12. extractionthe mixture was extracted with methylene chloride
  13. dry with materialThe organic phase was dried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationThe filtrate was concentrated under reduced pressure
  16. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-82cc0d7f22e94c1e825c8c96f0e3356b
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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