Methanol → 2-[(2,5-Dimethylphenoxy)methyl]-alpha-(methoxyimino)-N-methylbenzeneacetamide

HRID 273931Notes

Reaction equation

HRID 273931 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=O)[C:13]([NH:15][CH3:16])=[O:14].CO.Cl.[O:26]([NH2:28])[CH3:27]>O>[CH3:1][C:2]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[N:28][O:26][CH3:27])[C:13]([NH:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 110877922-[2-(2,5-dimethylphenoxymethyl)phenyl]-N-methyl-2-oxoacetamide

Product 1

HCID 544553462-[(2,5-Dimethylphenoxy)methyl]-alpha-(methoxyimino)-N-methylbenzeneacetamideYield 98.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2-[2-(2,5-dimethylphenoxymethyl)phenyl]-N-methyl-2-oxoacetamide (0.27 g, 0.9 mmol), added were methanol (2.0 ml) and methoxylamine hydrochloride (0.15 g, 1.8 mmol), and the reaction mixture was heated under reflux for 4 hours. After completion of the reaction, water (100 ml) was added to the reaction mixture which was then extracted with methylene chloride. The extract was 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-(2,5-dimethylphenoxymethyl)phenyl] -2-methoxyimino-N-methylacetamide (0.28 g; yield, 98.9%) as a mixture of E-form and Z-form.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 4 hours
  3. additionwas added to the reaction mixture which
  4. extractionwas then extracted with methylene chloride
  5. dry with materialThe extract was dried 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-fa6806cecbc54504aeb265e185871659
Source dataset
uspto-grants-1995_02
Patent number
US05387714

Reaction notes

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