Sodium Bicarbonate → HCID 86604807, compound

HRID 856238Notes

Reaction equation

HRID 856238 reaction equation
[N+]([C:4]1[NH:5][CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[N:8]=1)([O-])=O.[O:12]1[CH2:14][CH:13]1[CH2:15][NH:16][C:17](=[O:25])[O:18][C:19]1C=CC=C[CH:20]=1.C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)C.C(Cl)Cl>[N+:9]([C:7]1[N:8]=[C:4]2[N:5]([CH:6]=1)[CH2:14][CH:13]([CH2:15][NH:16][C:17](=[O:25])[O:18][CH2:19][CH3:20])[O:12]2)([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 11052496HCID 11052496, compoundHCID 178526857HCID 178526857, compound

Product 1

HCID 86604807HCID 86604807, compoundYield 11.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

2,4-Dinitro-1H-imidazole (0.678 g, 3.92 mmol) and phenyl oxiran-2-ylmethylcarbamate (1.04 g, 5.87 mmol) were dissolved in ethanol (20 ml). To the solution, sodium acetate (0.386 g, 4.70 mmol) was added followed by stirring under reflux 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 (methylene chloride/methanol=50/1) and treated with diisopropyl ether to afford ethyl (6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)carbamate (0.116 g, yield 11.6%) as a light brown solid.

Workup

  1. temperatureunder reflux overnight
  2. extractionthe solution was extracted with methylene chloride
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1)
  7. additiontreated with diisopropyl ether

Sources & evidence

ORD record
ord-111729e3229347cf88b9a36952d6a3f8
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…