Hydrogen Peroxide → alpha-(2,4-difluorophenyl)-N-[dimethyl(methoxymethyl) methyl]nitrone

HRID 636735Notes

Reaction equation

HRID 636735 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:11]([CH3:16])([CH3:15])[CH2:12][O:13][CH3:14].[OH:17]O.[Na+].[Cl-]>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[N+:10]([C:11]([CH3:16])([CH3:15])[CH2:12][O:13][CH3:14])[O-:17]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 21255704N-(2,4-difluorophenylmethyl)-N-[dimethyl(methoxymethyl)methyl]amine

Product 1

HCID 72602289alpha-(2,4-difluorophenyl)-N-[dimethyl(methoxymethyl) methyl]nitroneYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(2,4-difluorophenylmethyl)-N-[dimethyl(methoxymethyl)methyl]amine obtained in Example 14 (378.8 mg, 1.65 mmol) and Na2WO4 2H2O (84.3 mg, 0.256 mmol) in methanol (5 ml) was cooled to 0° C. in ice-water bath. To the mixture was added dropwise 31% H2O2 aqueous solution (439.3 mg, 4.00 mmol). After addition the mixture was gradually warmed to room temperature and stirred for 15 hours. The mixture was added to sat. NaCl aqueous solution and extracted three times with ethyl acetate and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (toluene/ethyl acetate=5/1) to give the title compound (204.8 mg; 51%).

Workup

  1. additionAfter addition the mixture
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationThe mixture was concentrated
  5. custompurified by silica gel chromatography (toluene/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-4d225aabeb784a0ca64a287642cac08b
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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