反应详情

To a suspension of 4-(methylsulfonyl)aniline hydrochloride (10 g, 48.1 mmol) in toluene (250 ml) at 0° C., trimethylaluminum (2M solution in toluene, 36.1 ml, 72.2 mmol) was added over 10 minutes. The reaction mixture was warmed to room temperature and stirred for 2.5 hours. A solution of 4-cyanopyridine (10 g, 96.2 mmol) in toluene (250 ml) was added over 10 minutes and the mixture was heated to 70° C. After 24 hours, the reaction mixture was cooled to room temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue was washed with a mixture of methylene chloride/methanol and later with methanol. The combined filtrates were concentrated and the resulting yellowish solid was stirred with ethyl acetate and filtered. The pale yellow solid (4.8 g, 36%) was used in the next reaction without further purification. Anal. Calc'd. for C13H14N3SClO2H2O: C, 47.34, H, 4.89, N, 12.74, S, 9.72. Found: C, 47.69, H, 4.35, N, 12.77, S, 9.74.

1. temperaturethe mixture was heated to 70° C
2. waitAfter 24 hours
3. temperaturethe reaction mixture was cooled to room temperature
4. filtrationAfter filtration
5. washthe residue was washed with a mixture of methylene chloride/methanol and later with methanol
6. concentrationThe combined filtrates were concentrated
7. stirringthe resulting yellowish solid was stirred with ethyl acetate
8. filtrationfiltered
9. customThe pale yellow solid (4.8 g, 36%) was used in the next reaction without further purification