반응 #215719

반응 방정식

2-Fluoro-4-chloro-5-cyclohexyloxyaniline

3,4,5,6-tetrahydrophthalic anhydride

acetic acid

→

N-(2-fluoro-4-chloro-5-cyclohexyloxyphenyl) 3,4,5,6-tetrahydrophthalimide

수율 70.0%

용매

water

반응 조건

후처리

1. 1
   온도heated for 15 hours
2. 2
   온도while refluxing
3. 3
   기타After completion of the reaction
4. 4
   추출extracted with ethyl acetate (20 ml×3)
5. 5
   세척washed with water
6. 6
   건조a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
7. 7
   기타The drying agent was separated by filtration
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   기타to obtain a crude product (332 mg)
10. 10
    기타The product was purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=19/1)

실험 절차

2-Fluoro-4-chloro-5-cyclohexyloxyaniline (213 mg, 0.874 mmol), 3,4,5,6-tetrahydrophthalic anhydride (134 mg, 0.874 mmol) and acetic acid (10 ml) were charged into a 50 cc round-bottom flask, and heated for 15 hours while refluxing. After completion of the reaction, the reaction solution was cooled to room temperature, water (50 ml) was added thereto, and extracted with ethyl acetate (20 ml×3). The organic layers were combined, washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration and the solvent was distilled off under reduced pressure to obtain a crude product (332 mg). The product was purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=19/1) to obtain N-(2-fluoro-4-chloro-5-cyclohexyloxyphenyl) 3,4,5,6-tetrahydrophthalimide as a white solid (230 mg, 0.609 mmol, 70% yield). By recrystallization of the product from hexane/chloroform, it was isolated as white needle crystals.

출처