Water → Diethyl[2-(4-nitrophenoxy)ethyl]amine

HRID 379698

Reaktionsgleichung

Reaktionsgleichung von HRID 379698
O.O.[N+:3]([C:6]1[CH:13]=[CH:12][C:9]([O:10][Na])=[CH:8][CH:7]=1)([O-:5])=[O:4].Cl.[CH2:15]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19]Cl)[CH3:16].C(=O)([O-])[O-].[K+].[K+].O>C1(C)C(C)=CC=CC=1>[CH2:15]([N:17]([CH2:21][CH2:22][O:10][C:9]1[CH:12]=[CH:13][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1)[CH2:18][CH3:19])[CH3:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 178526976HCID 178526976, Verbindung

Produkt 1

HCID 88294Diethyl[2-(4-nitrophenoxy)ethyl]amineAusbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

4-Nitrophenoxy sodium dihydrate (29.39 g), 2-(diethylamino)ethylchloride hydrochloride (25.60 g), potassium carbonate (30.17 g) and water (60 ml) were added into xylene (100 ml) and the mixture was heat-refluxed for 2 hours while mixing and continuously removing water by azeotropic distillation. After reaction, insolubles were removed by filtration. Filtrate was added with ethyl acetate (100 ml) and extracted 3 times with 1N HCl (100 ml). Aqueous layer was adjusted to pH 10 with 1N sodium hydroxide and oily substance separated was extracted 3 times with ethyl acetate (100 ml). Ethyl acetate solution was dehydrated with anhydrous magnesium sulfate and concentrated to obtain N,N-diethyl-2-(4-nitrophenoxy)ethylamine (28.19 g) as color-less oily substance.

Aufarbeitung

  1. temperaturethe mixture was heat-refluxed for 2 hours
  2. additionwhile mixing
  3. distillationcontinuously removing water by azeotropic distillation
  4. customAfter reaction, insolubles
  5. customwere removed by filtration
  6. additionFiltrate was added with ethyl acetate (100 ml)
  7. extractionextracted 3 times with 1N HCl (100 ml)
  8. customseparated
  9. extractionwas extracted 3 times with ethyl acetate (100 ml)
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5642302a26bc4e7a83e80cc162e8c81c
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300368B1

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