Reaktion #453496

Reaktionsgleichung

hydrochloric acid

ethyl 3-amino-4,4,4-trifluorocrotonate

1,8-diazabicyclo[5.4.0]-7-undecene

4-chloro-2-ethyl-6-fluoro-7-phenoxycarbonylaminobenzofuran

→

desired product

Ausbeute 44.0%

3-(4-chloro-2-ethyl-6-fluorobenzofuran-7-yl)-6-trifluoromethyluracil

Ausbeute 44.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas gradually added
2. 2
   Sonstigeat room temperature
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed sequentially with water
5. 5
   Trocknena saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   SonstigeThen, the obtained residue was purified by silica gel column chromatography

Vorschrift

80 ml of N,N-dimethylformamide was added to 5.8 g (32 mmol) of ethyl 3-amino-4,4,4-trifluorocrotonate and 6.6 g (43 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene, and 9.6 g (29 mmol) of 4-chloro-2-ethyl-6-fluoro-7-phenoxycarbonylaminobenzofuran was gradually added thereto at room temperature. After stirring at 60° C. for 8 hours, the reaction solution was poured into a 10% hydrochloric acid aqueous solution and acidified, and then extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 4.8 g (yield: 44%) of the desired product as white crystals. Melting point: 154-155° C.

Quelle