Dimethylformamide → methyl 4-[3-[N-(4chlorophenyl)amino]propoxy]-alpha-methylcinnamate
Reaktionsgleichung
C(=O)([O-])O.[Na+].[Cl:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.CN(C=O)C.Cl[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:36]=[CH:35][C:27]([CH:28]=[C:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=1>O>[Cl:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][CH2:20][CH2:21][CH2:22][O:23][C:24]2[CH:36]=[CH:35][C:27]([CH:28]=[C:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=2)=[CH:9][CH:8]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
Sodium hydrogen carbonate (3.5 g), 4-chloroaniline (10.45 g) and DMF (50 ml) were added to methyl 4-(3-chloropropoxy)-α-methylcinnamate (11 g), and the mixture was stirred at 100° C. overnight. After the reaction mixture was allowed to cool, water (200 ml) was added thereto, and further the mixture was stirred at room temperature for 30 minutes. The insoluble product was collected by filtration, washed well with water, and was added cold methanol (20ml) thereto, and the mixture was stirred. The resulting crystal was collected by filtration to give methyl 4-[3-[N-(4chlorophenyl)amino]propoxy]-α-methylcinnamate (8 g). mp. 62°-64° C.
Aufarbeitung
- temperatureto cool
- stirringfurther the mixture was stirred at room temperature for 30 minutes
- filtrationThe insoluble product was collected by filtration
- washwashed well with water
- additionwas added cold methanol (20ml)
- stirringthe mixture was stirred
- filtrationThe resulting crystal was collected by filtration
Quellen und Nachweise
- ORD-Eintrag
- ord-f614b82489724963b16de0b6862bc139
- Quelldatensatz
- uspto-grants-1991_03
- Patentnummer
- US04999378
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