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Ethylenediamine → HCID 57548171, Verbindung

HRID 1993909
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1993909
C[Al](C)C.[CH2:5]([NH2:8])[CH2:6][NH2:7].C(O[C:12](=O)[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)C>C1(C)C=CC=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][C:12]2[NH:7][CH2:6][CH2:5][N:8]=2)=[CH:16][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 3301EthylenediamineHCID 10921830Ethyl 3-(4-chlorophenyl)propanoateHCID 16682925Trimethylaluminum

Produkt 1

HCID 57548171HCID 57548171, VerbindungAusbeute 50,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel4×

Versuchsvorschrift

To dry toluene (4 ml) under an inert atmosphere at 0° C. was added a toluene solution of trimethylaluminium (2.45 ml, 4.89 mmol, 2 M solution). A solution of ethylenediamine (0.30 ml, 4.89 mmol) in toluene (1.5 ml) was then added dropwise and the reaction mixture was then allowed to warm to room temperature and stirred for 1 h at this temperature before being re-cooled to 0° C. To this mixture was added dropwise a solution of 3-(4-chloro-phenyl)-propionic acid ethyl ester (0.52 g, 2.45 mmol) in toluene (3 ml). The reaction mixture was then heated at 95° C. for 45 min and then cooled first to room temperature and finally to 0° C. The mixture was quenched by dropwise addition of methanol (1 ml) and when all gas evolution had ceased the mixture was diluted with water and extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulphate, filtered and concentrated in vacuo. The residue was triturated in ether to yield a white solid (0.26 g, 50%) which was collected by filtration; MS (ISP): 211.0, 209.2 ([M+H]+.).

Aufarbeitung

  1. temperaturebefore being re-cooled to 0° C
  2. temperatureThe reaction mixture was then heated at 95° C. for 45 min
  3. temperaturecooled first to room temperature and finally to 0° C
  4. customThe mixture was quenched by dropwise addition of methanol (1 ml) and when all gas evolution
  5. additionwas diluted with water
  6. extractionextracted twice with ethyl acetate
  7. dry with materialThe combined organic extracts were dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated in ether

Quellen und Nachweise

ORD-Eintrag
ord-076653fa99bd42c1bd0ca6531b22e581
Quelldatensatz
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07652055B2

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