Reaktion #45705

Reaktionsgleichung

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile

diisopropylethylamine

ethyl 3-(methylamino)propionate hydrochloride

→

compound

Ausbeute 81.0%

Ethyl 3-[N-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)methylamino]propionate

Ausbeute 81.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter heated
2. 2
   Temperaturunder reflux for 3 hours
3. 3
   WaschenAfter washed with water
4. 4
   Trocknendrying over anhydrous sodium sulfate
5. 5
   Sonstigethe solvent was evaporated away under reduced pressure
6. 6
   Sonstigethe resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70; 1)
7. 7
   Sonstigeagain purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1)

Vorschrift

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (0.49 g, 1.71 mmol), diisopropylethylamine (0.70 ml, 4.12 mmol) and ethyl 3-(methylamino)propionate hydrochloride (I-159) (0.32 g, 1.91 mmol) were dissolved in dichloromethane (15 ml). After heated under reflux for 3 hours, this was diluted with dichloromethane. After washed with water and drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70; 1), then again purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1) to obtain the entitled compound (0.53 g, 81%) as a brown oil.

Quelle