تفاعل #80620

معادلة التفاعل

4-cyanopyridine

4-(methylsulfonyl)aniline hydrochloride

trimethylaluminum

→

N-[4-(methylsulfonyl) phenyl]-4-pyridinecarboximidamide

المذيبات

toluene

chloroform

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was heated to 70° C
2. 2
   workup.WAITAfter 24 hours
3. 3
   درجة الحرارةthe reaction mixture was cooled to room temperature
4. 4
   ترشيحAfter filtration
5. 5
   غسيلthe residue was washed with a mixture of methylene chloride/methanol and later with methanol
6. 6
   تركيزThe combined filtrates were concentrated
7. 7
   workup.STIRRINGthe resulting yellowish solid was stirred with ethyl acetate
8. 8
   ترشيحfiltered
9. 9
   أخرىThe pale yellow solid (4.8 g, 36%) was used in the next reaction without further purification

الإجراء التجريبي

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.

المصدر