Dimethylformamide → Dimoxystrobin

HRID 273933

Reaktionsgleichung

Reaktionsgleichung von HRID 273933
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]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 72672,5-DimethylphenolHCID 11430Potassium CarbonateHCID 15239358HCID 15239358, Verbindung

Produkt 1

HCID 10936292DimoxystrobinAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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-dimethylphenoxymethyl)phenyl]-2-methoxyimino-N-methylacetamide (0.57 g) as colorless crystals (yield, 69.8%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a6ab935836b04765aa14a6c1400590ae
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387714

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