Dimethylformamide → Dimoxystrobin

HRID 1938889Notes

Reaction equation

HRID 1938889 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[N:14]\[O:15][CH3:16])/[C:10]([NH:12][CH3:13])=[O:11].CN(C=O)C.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=1[OH:30].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=1[O:30][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[N:14]\[O:15][CH3:16])/[C:10]([NH:12][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72672,5-DimethylphenolHCID 11430Potassium CarbonateHCID 15239358(2E)-2-[2-(bromomethyl)phenyl]-2-methoxyimino-N-methylacetamide

Product 1

HCID 10936292DimoxystrobinYield 69.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To (E)-2-(2-bromomethylphenyl)-2-methoxyimino-N-methylacetamide (0.72 g, 2.5 mmol), added were dry DMF (5.0 ml), 2,5-dimethylphenol (0.46 g, 3.75 mmol) and potassium carbonate (0.69 g, 5.0 mmol), and the reaction mixture was stirred at room temperature for 4 hours. Then, water (100 ml) was added to the reaction mixture which was then extracted with ethyl acetate (100 ml). The extract was washed with water (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give (E)-2-[2-(2,5-dimethylphenoxy-methyl)phenyl]-2-methoxyimino-N-methylacetamide (0.57 g) as colorless crystals (yield, 69.8%).

Workup

  1. extractionwas then extracted with ethyl acetate (100 ml)
  2. washThe extract was washed with water (100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  6. customto give

Sources & evidence

ORD record
ord-056bc84b932149cba62561cf9c26a478
Source dataset
uspto-grants-1997_12
Patent number
US05693859

Reaction notes

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