반응 #80625

반응 방정식

6-methyl-2-cyanopyridine

4-(methylsulfonyl)aniline hydrochloride

trimethylaluminum

→

2-methyl-N-[4-(methylsulfonyl)phenyl]-6-pyridinecarboximidamide

용매

toluene

chloroform

toluene

반응 조건

후처리

1. 1
   온도the mixture was heated to 85°-90° C
2. 2
   workup.WAITAfter 24 hours
3. 3
   온도the reaction mixture was cooled to room temperature
4. 4
   여과After filtration
5. 5
   세척the residue was washed with a mixture of methylene chloride/methanol and later with methanol
6. 6
   농축The combined filtrates were concentrated
7. 7
   workup.STIRRINGthe resulting yellowish solid was stirred with hexane and ethyl acetate (1000 ml)
8. 8
   여과filtered
9. 9
   기타The white solid (5.1 g, 87%) was used in the next reaction without further purification

실험 절차

To a suspension of 4-(methylsulfonyl)aniline hydrochloride (4.2 g, 20.3 mmol) in toluene (100 ml) at 0° C., was added trimethylaluminum (2M solution in toluene, 12 ml, 24 mmol) over 10 minutes. The reaction mixture was warmed to room temperature and stirred for 2 hours. A solution of 6-methyl-2-cyanopyridine (3.6 g, 30.5 mmol) in toluene (100 ml) was added over 10 minutes and the mixture was heated to 85°-90° 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 hexane and ethyl acetate (1000 ml) and filtered. The white solid (5.1 g, 87%) was used in the next reaction without further purification. Anal. Calc'd. for C14H16N3SClO2H2O: C, 51.05, H, 5.02, N, 12.76. Found C, 50.97, H, 4.78, N, 12.80.

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