Reaktion #45650

Reaktionsgleichung

hydrochloric acid

trimethylamine

dimethylamine hydrochloride

ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

→

compound

Ausbeute 67.0%

4-Cyano-7-fluoro-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

Ausbeute 67.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the reaction liquid
2. 2
   Temperaturwith cooling with ice
3. 3
   workup.STIRRINGby stirring at room temperature
4. 4
   Sonstigethe reaction liquid
5. 5
   Extraktionwas extracted with chloroform
6. 6
   Trocknendried oil anhydrous magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenthe filtrate was concentrated under reduced pressure
9. 9
   Waschenwashed in diethyl ether

Vorschrift

Under nitrogen atmosphere, trimethylamine (1.03 M n-hexane solution, 2.25 ml, 2.31 mmol) was dropwise added at room temperature to a dichloromethane (3 ml) solution of dimethylamine hydrochloride (189 mg, 2.31 mmol), followed by stilling for 25 minutes. Subsequently, a dichloromethane (2 ml) solution of ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (250 mg, 771 μmol) was dropwise added, followed by stirring for 17 hours. After the reaction, aqueous 1N hydrochloric acid solution was added to the reaction liquid with cooling with ice, followed by stirring at room temperature, and the reaction liquid was extracted with chloroform. Next, the obtained organic layers were combined, dried oil anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was suspended and washed in diethyl ether to obtain the entitled compound (167 mg, 67%) as a white solid.

Quelle