Hydrogen Peroxide → 2-(2-Phenoxyphenyl)-2-methoxyiminoacetamide

HRID 1779733Notes

Reaction equation

HRID 1779733 reaction equation
[O:1]([C:8]1[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=1[C:10]([C:14]#[N:15])=[N:11][O:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-:21].[Na+].[Na+].OO.CCOCC>CC(C)=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:1]([C:8]1[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=1[C:10](=[N:11][O:12][CH3:13])[C:14]([NH2:15])=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 541653652-Phenoxy-alpha-methoxyiminobenzyl cyanide

Product 1

HCID 539671372-(2-Phenoxyphenyl)-2-methoxyiminoacetamideYield 455.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Procedure

2-Phenoxy-α-methoxyiminobenzyl cyanide (E/Z=21/79)(1.26 g, 5 mmol) was dissolved in acetone (5 ml). Sodium carbonate (0.11 g, 1 mmol), tetra-n-butylammonium bromide (0.08 g, 0.25 mmol), 30% aqueous hydrogen peroxide solution (1.13 g, 10 mmol) were added, and the mixture was heated under reflux for 5 hours. After completion of the reaction, ether (50 ml) was added. The mixture was washed with a saturated aqueous solution of sodium thiosulfate, water and saturated brine, and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(2-phenoxyphenyl)-2-methoxyiminoacetamide (1.23 g, Yield: 91.0%, E/Z=23/77).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. additionwas added
  4. washThe mixture was washed with a saturated aqueous solution of sodium thiosulfate, water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-c84879de4d85423a94d876e34042fa77
Source dataset
uspto-grants-1997_05
Patent number
US05627284

Reaction notes

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