Ethylenediamine → N-(5-pyrimidinylmethyl)ethylenediamine

HRID 231188

Reaktionsgleichung

Reaktionsgleichung von HRID 231188
[CH2:1]([NH2:4])[CH2:2][NH2:3].[CH:5]([C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1)=O>C1C=CC=CC=1>[N:9]1[CH:8]=[C:7]([CH2:5][NH:3][CH2:2][CH2:1][NH2:4])[CH:12]=[N:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 3301EthylenediamineHCID 2761034Pyrimidine-5-carboxaldehyde

Produkt 1

HCID 13910892N-(5-pyrimidinylmethyl)ethylenediamineAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Ethylenediamine (60 g) was dissolved in benzene (200 ml), and 5-formylpyrimidine (21.6 g) was added at room temperature. Subsequently, the mixture was heated, and refluxed for 3 hours while removing water as an azeotrope. After the reaction, benzene and the excess of ethylenediamine were distilled off under reduced pressure. The residue was dissolved in ethanol (200 ml). Sodium borohydride (8.4 g) was added portionwise to this solution at room temperature, and subsequently the mixture was stirred at room temperature for 5 hours. Ethanol was distilled off under reduced pressure. Dichloromethane (100 ml) was added to the residue, and a dichloromethane-soluble portion was separated. Dichloromethane was distilled off from the dichloromethane layer under reduced pressure to give N-(5-pyrimidinylmethyl)ethylenediamine (25.8 g) as a colorless oil. nD25 =1.5532.

Aufarbeitung

  1. temperatureSubsequently, the mixture was heated
  2. temperaturerefluxed for 3 hours
  3. customwhile removing water as an azeotrope
  4. customAfter the reaction, benzene
  5. distillationthe excess of ethylenediamine were distilled off under reduced pressure
  6. dissolutionThe residue was dissolved in ethanol (200 ml)
  7. additionSodium borohydride (8.4 g) was added portionwise to this solution at room temperature
  8. distillationEthanol was distilled off under reduced pressure
  9. additionDichloromethane (100 ml) was added to the residue
  10. customa dichloromethane-soluble portion was separated
  11. distillationDichloromethane was distilled off from the dichloromethane layer under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-44fd6bbfb3c74f06b41c5c7cac8e859b
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845106

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