Реакция #453496

Уравнение реакции

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

Выход 44.0%

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

Выход 44.0%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas gradually added
2. 2
   Другоеat room temperature
3. 3
   Экстракцияextracted with ethyl acetate
4. 4
   ПромывкаThe organic layer was washed sequentially with water
5. 5
   Сушкаa 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
   ДругоеThen, the obtained residue was purified by silica gel column chromatography

Методика

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.

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