Ethylenediamine → HCID 22909780, Verbindung

HRID 1379166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1379166
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23]Br)=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(=O)([O-])[O-].[K+].[K+].[CH2:34]([NH2:37])[CH2:35][NH2:36]>CS(C)=O.ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH:36][CH2:35][CH2:34][NH2:37])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Komponenten

6

Edukt 3

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 22909785HCID 22909785, Verbindung

Produkt 1

HCID 22909780HCID 22909780, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.35 g (0.81 mmol) of N-{3-(3,4-dimethylphenyl)propyl}-4-(2-bromoethoxy)-3-methoxyphenylacetamide obtained in step 1 of Example 2 was dissolved in 3 ml of dimethylsulfoxide and 0.56 g (4.02 mmol) of potassium carbonate was added thereto. To this mixture, 0.48 g (8.06 mmol) of ethylenediamine was slowly added at room temperature, followed by stirring at room temperature for 4 hours. The reaction mixture was diluted with 40 ml of dichloromethane, washed with water and acidified with 1N HCl and the aqueous layer was separated. The aqueous layer was basified with hydrogen peroxide, extracted with 40 ml of dichloromethane, dried and the solvent was removed under a reduced pressure. The residue was triturated with a mixture of dichloromethane and hexane(1:2) to obtain 0.10 g of the title compound as a white solid(yield: 30%).

Aufarbeitung

  1. washwashed with water
  2. customthe aqueous layer was separated
  3. extractionextracted with 40 ml of dichloromethane
  4. customdried
  5. customthe solvent was removed under a reduced pressure
  6. customThe residue was triturated with a mixture of dichloromethane and hexane(1:2)

Quellen und Nachweise

ORD-Eintrag
ord-3bb7f86a32174dd6ba4246946859a574
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05670546

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