反应详情

A mixed liquid comprising 25 g of 5-chloro-2-nitrobenzic acid, 25 ml of toluene, 22.2 g of thionyl chloride and 0.1 ml of dimethylformamide was refluxed with heating for 1 hour to prepare acid chloride. 18.0 g of triethylamine was added to a mixed solution comprising 13.75 g of 1-cyclopropylethylamine and 375 ml of tetrahydrofuran and cooled with ice. The above prepared acid chloride was dissolved in 30 ml of toluene and dropwise added under cooling with ice. After completion of dropwise addition, reaction was carried out at room temperature for 15 hours. After completion of the reaction, the reaction mixture was poured to water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 25 g of the pale yellow desired product (melting point: 137 to 141° C.).

1. temperaturewas refluxed
2. temperaturewith heating for 1 hour
3. temperaturecooled with ice
4. additiondropwise added
5. temperatureunder cooling with ice
6. additionAfter completion of dropwise addition, reaction
7. customAfter completion of the reaction
8. extractionfollowed by extraction with ethyl acetate
9. washThe organic layer was washed with a saturated sodium chloride aqueous solution
10. dry with materialdried over sodium sulfate, and ethyl acetate
11. distillationwas distilled off under reduced pressure
12. customThe residue was purified by silica gel column chromatography