Pyridine → HCID 57301716, Verbindung

HRID 2413355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2413355
S(Cl)([Cl:3])=O.[CH3:5][C:6](=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:13][CH:12]=1)[C:7](O)=[O:8].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:5][C:6](=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:13][CH:12]=1)[C:7]([Cl:3])=[O:8]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 54447167HCID 54447167, Verbindung

Produkt 1

HCID 57301716HCID 57301716, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

5 g of thionyl chloride was added dropwise to a mixture of 6 g of 2-methyl-3-[4-(3-pyridyloxy)phenyl]propenoic acid, 80 ml of pyridine and 50 ml of chloroform under ice-cooling with stirring, followed by stirring for one hour to obtain a solution of 2-methyl-3-[4-(3-pyridyloxy)phenyl]propenoic acid chloride. 8 g of cyclohexylamine was added to the solution, and the mixture was stirred for one hour and poured into water. The mixture was rendered basic with sodium carbonate, and the organic layer was separated by filtration, washed with water and dried over magnesium sulfate. The solvent was distilled off and the resulting oily substance was purified by silica gel chromatography (eluted with chloroform-diethyl ether, 1:2 by volume). The resulting crystals were converted into the hydrochloride in the same manner as described in Example 4 and recrystallized from a mixture of ethanol and diethyl ether to obtain 4.5 g (51% yield) of N-cyclohexyl-2-methyl-3-[4-(3-pyridyloxy)phenyl]propenamide hydrochloride having a melting point of 162°-166° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringby stirring for one hour

Quellen und Nachweise

ORD-Eintrag
ord-1167aa9c45ab42008d95eefa49961bcf
Quelldatensatz
uspto-grants-1985_01
Patentnummer
US04496735

Notizen zur Reaktion

Wird geladen…