Dimethyl Sulfate → (2E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide

HRID 376037

Reaktionsgleichung

Reaktionsgleichung von HRID 376037
[OH:1]/[N:2]=[C:3](\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:4]([NH:6][CH3:7])=[O:5].[C:21](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O.[OH-].[Na+]>C1(C)C=CC=CC=1.CC(C)=O>[CH3:21][O:1]/[N:2]=[C:3](\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:4]([NH:6][CH3:7])=[O:5]

Komponenten

7

Edukt 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 9816878(E)-2-(Hydroxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide

Produkt 1

HCID 5483872(2E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamideAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To E-2-hydroxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide (10.00 g, 0.037 mole) were added acetone (200 ml), potassium carbonate (15.34 g, 0.111 moles) and dimethylsulfate (9.33 g, 0,074 moles) and the mixture was stirred at room temperature for 9 hours. After completion of the reaction, the reaction mixture was filtered, washed with acetone and concentrated under reduced pressure. The oil thus obtained was dissolved in toluene (50 ml) and to this was added an aqueous 1N sodium hydroxide solution (50 ml), followed by stirring at room temperature for 30 minutes. The mixture was extracted with toluene, washed with water and concentrated, and then the resulting residue was recrystallized (methanol/water) to obtain E-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide (9.93 g, yield: 94.4%) as colorless crystals (melting point: 81.5°-83° C.).

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. washwashed with acetone
  4. concentrationconcentrated under reduced pressure
  5. customThe oil thus obtained
  6. stirringby stirring at room temperature for 30 minutes
  7. extractionThe mixture was extracted with toluene
  8. washwashed with water
  9. concentrationconcentrated
  10. customthe resulting residue was recrystallized (methanol/water)

Quellen und Nachweise

ORD-Eintrag
ord-df680024924a45c39dbde757034b9732
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488159

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