Sodium Bicarbonate → HCID 86604808, compound

HRID 856239Notes

Reaction equation

HRID 856239 reaction equation
[N+]([C:4]1[NH:5][CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[N:8]=1)([O-])=O.[CH3:12][C:13]1([CH2:16][NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15][O:14]1.C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)C.C(Cl)Cl>[CH3:15][C:13]1([CH2:16][NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:14][C:4]2=[N:8][C:7]([N+:9]([O-:11])=[O:10])=[CH:6][N:5]2[CH2:12]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 86604809HCID 86604809, compoundHCID 178526857HCID 178526857, compound

Product 1

HCID 86604808HCID 86604808, compoundYield 4.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

2,4-Dinitro-1H-imidazole (3 g, 19 mmol) and benzyl (2-methyloxiran-2-ylmethyl)carbamate (4.31 g, 19 mmol) were dissolved in ethanol (20 ml). To the solution, sodium acetate (1.56 g, 19.0 mmol) was added followed by stirring at 70° C. overnight. To the reaction mixture, a saturated sodium hydrogencarbonate solution and methylene chloride were added, and the solution was extracted with methylene chloride. The organic phase was dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1, methylene chloride/methanol=50/1) and recrystallized from ethyl acetate-methylene chloride to afford benzyl (2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)carbamate (0.298 g, yield 4.7%) as a colorless solid.

Workup

  1. extractionthe solution was extracted with methylene chloride
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1, methylene chloride/methanol=50/1)
  6. customrecrystallized from ethyl acetate-methylene chloride

Sources & evidence

ORD record
ord-1e915407133c487a9ba3b385e9dd180d
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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