Reaktion #45681

Reaktionsgleichung

sodium hydrogencarbonate

methylamine hydrochloride

triethylamine

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

→

compound

Ausbeute 82.0%

2-(Diethylamino)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Ausbeute 82.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Sonstigethe reaction liquid
3. 3
   SonstigeThe aqueous layer was separated
4. 4
   Extraktionthis was extracted twice with dichloromethane
5. 5
   Waschenwashed with saturated brine
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   SonstigeThe insoluble matter was separated by filtration
8. 8
   Sonstigethe solvent was evaporated away
9. 9
   Sonstigethe resulting residue was purified by preparative TLC (eluent, chloroform)

Vorschrift

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (100 mg, 0.35 mmol) was dissolved in dichloromethane (5 ml) in a sealed tube, then methylamine hydrochloride (26 mg, 0.38 mmol) and triethylamine (122 μl, 0.87 mmol) were successively added. The reaction system was heated at 45° C. for 3 hours. After cooling to room temperature, the reaction liquid was fractionated with dichloromethane and an aqueous saturated sodium hydrogencarbonate solution. The aqueous layer was separated, this was extracted twice with dichloromethane. The organic layers were combined, washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform) to obtain the entitled compound (80 mg, 82%) as a white solid.

Quelle