Sodium Chloride → N-4-Chlorocinnamyl-1,2-phenylenediamine

HRID 5734

Reaktionsgleichung

Reaktionsgleichung von HRID 5734
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Cl:9][C:10]1[CH:19]=[CH:18][C:13]([CH:14]=[CH:15][CH2:16]Cl)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>CN(C)C=O.O>[Cl:9][C:10]1[CH:19]=[CH:18][C:13]([CH:14]=[CH:15][CH2:16][NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH2:8])=[CH:12][CH:11]=1

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 53728250p-Chlorocinnamyl chloride

Produkt 1

HCID 54229126N-4-Chlorocinnamyl-1,2-phenylenediamineAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

19.6 g of 1,2-phenylenediamine was dissolved in 300 ml of dimethylformamide, to the solution were added 11.3 g of the above-prepared 4-chlorocinnamyl chloride crystals and 12.5 g of potassium carbonate at a room temperature with stirring, and the mixture was stirred for 48 hours under the same condition. After adding water and sodium chloride, the reaction mixture was extracted twice with 1000 ml of chloroform, and the extract was dried over magnesium sulfate and evaporated to remove the solvent under a reduced pressure. Resulting residue was applied to a silica gel column and eluted with hexane/ethyl acetate (3:1), to obtain 12.85 g of the title compound as colorless crystals.

Aufarbeitung

  1. stirringthe mixture was stirred for 48 hours under the same condition
  2. extractionthe reaction mixture was extracted twice with 1000 ml of chloroform
  3. dry with materialthe extract was dried over magnesium sulfate
  4. customevaporated
  5. customto remove the solvent under a reduced pressure
  6. washeluted with hexane/ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-c09855ed64714736b79c8d5024c94a04
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245034

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