Hydrogen Peroxide → HCID 131732894, compound

HRID 2166983Notes

Reaction equation

HRID 2166983 reaction equation
[NH2:1][C:2](=[N:11][O:12][CH:13]([CH3:15])[CH3:14])[C:3](=[N:6][O:7][CH:8]([CH3:10])[CH3:9])[C:4]#[N:5].OO.C(=O)([O-])[O-:19].[Na+].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[NH2:1][C:2](=[N:11][O:12][CH:13]([CH3:15])[CH3:14])[C:3](=[N:6][O:7][CH:8]([CH3:9])[CH3:10])[C:4]([NH2:5])=[O:19]

Participants

7

Reactant 4

HCID 784Hydrogen Peroxide3×HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 121292342HCID 121292342, compound

Product 1

HCID 131732894HCID 131732894, compoundYield 889.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 887MethanolSolvent

Procedure

To a methanol solution (140 ml) of 29.0 g (137 mM) of 3-amino-2,3-bis(isopropoxyimino)propionitrile were added, at room temperature, 47 g (415 mM) of a 30% aqueous hydrogen peroxide solution, 1.5 g (15 mM) of sodium carbonate and 2.3 g (7.1 mM) of tetrabutylammonium bromide. Stirring was conducted at room temperature for 4 hours. Since the raw materials remained, further 24 g (212 mM) of a 30% aqueous hydrogen peroxide solution was added, followed by stirring at room temperature for 3 hours. Excessive hydrogen peroxide was treated with an aqueous sodium thiosulfate solution. The solvent was distilled off under reduced pressure. Water was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer obtained was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered to remove inorganic matter. The solvent was distilled off under reduced pressure. The crystal obtained was washed with a 1:2 mixed solution of diisopropyl ether and n-hexane to obtain 29.0 g (yield: 92%) of the title compound.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionWater was added to the resulting residue
  4. extractionfollowed by extraction with ethyl acetate
  5. customThe organic layer obtained
  6. washwas washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customto remove inorganic matter
  10. distillationThe solvent was distilled off under reduced pressure
  11. customThe crystal obtained
  12. washwas washed with a 1:2 mixed solution of diisopropyl ether and n-hexane

Sources & evidence

ORD record
ord-a140ce6aff4d4f5a827335f299bf6bd3
Source dataset
uspto-grants-2015_06
Patent number
US09044013B2

Reaction notes

Loading…