反应详情

3.1 g of magnesium turnings, 10 ml of ethyl ether and several pieces of iodide were placed in a flask under a nitrogen gas, and the mixture was refluxed to fade out the color caused by iodide. 90 ml of an ethyl ether solution containing 20 g of cyclohexyl bromide was added dropwise over a 30-minute period under reflux with stirring. The temperature of the reaction solution was returned to room temperature, 40 ml of a tetrahydrofuran solution containing 4.8 g of 2-aminobenzonitrile was added dropwise over a 30-minute period, and the mixture was stirred for 30 minutes. 150 ml of an aqueous 1N hydrochloric acid solution was cautiously added, and the mixture was neutralized with a dilute aqueous sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was washed, in turn, with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=20:1) and recrystallized from ethyl acetate-n-hexane to give 6.2 g of 2-cyclohexylcarbonylaniline.

1. temperaturethe mixture was refluxed
2. additionwas added dropwise over a 30-minute period
3. temperatureunder reflux
4. customwas returned to room temperature
5. additionwas added dropwise over a 30-minute period
6. stirringthe mixture was stirred for 30 minutes
7. extractionextracted with ethyl acetate
8. washThe ethyl acetate layer was washed, in turn, with water
9. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
10. customThe solvent was evaporated
11. customthe resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=20:1)
12. customrecrystallized from ethyl acetate-n-hexane