Hydroxylamine → 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-hydroxyimino-N-methylacetamide

HRID 1857815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1857815
CO.[NH2:3][OH:4].[CH2:5]([O:7][CH:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=O)[C:19]([NH:21][CH3:22])=[O:20])[CH3:9])[CH3:6]>O>[CH2:5]([O:7][CH:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[N:3][OH:4])[C:19]([NH:21][CH3:22])=[O:20])[CH3:9])[CH3:6]

Komponenten

5

Edukt 3

HCID 787HydroxylamineHCID 887MethanolHCID 154837862-[2-{(1-ethoxyethyl)oxymethyl}phenyl)-N-methyl-2-oxoacetamide

Produkt 1

HCID 738666042-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-hydroxyimino-N-methylacetamideAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Methanol (4 ml) and 50% aqueous hydroxylamine solution (0.4 g, 0.006 mol) were added to 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-N-methyl-2-oxoacetamide (0.53 g, 0.002 mol). The mixture was stirred under reflux for 5 hours. After completion of the reaction, water (100 ml) was added, and the mixture was extracted with dichloromethane (50 ml) twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-hydroxyimino-N-methylacetamide (Isomer A: 0.21 g (Yield: 37.5%), colorless oil; Isomer B: 0.14 g (Yield: 25.0%), colorless crystals).

Aufarbeitung

  1. temperatureunder reflux for 5 hours
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane (50 ml) twice
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ea2648f3a65e43a18e2f62bff33909a0
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06147231

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