반응 #80637

반응 방정식

2-thiophenecarbonitrile

4-(methylsulfonyl)aniline

trimethylaluminum

→

N-[4-(methylsulfonyl) phenyl]-2-thiophenecarboximidamide

용매

toluene

chloroform

toluene

반응 조건

후처리

1. 1
   온도the mixture was heated to 80°-85° C
2. 2
   workup.WAITAfter 16 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 yellow solid was stirred with ethyl acetate
8. 8
   여과filtered
9. 9
   기타The pale yellow solid (9.8 g, 57%) was used in the next reaction without further purification

실험 절차

To a suspension of 4-(methylsulfonyl)aniline (10.4 g, 61.1 mmol) in toluene (400 ml) at 0° C., trimethylaluminum (2M solution in toluene, 46.8 ml, 91.6 mmol) was added over 15 minutes. The reaction mixture was warmed to room temperature and stirred for 2 hours. A solution of 2-thiophenecarbonitrile (10.0 g, 91.6 mmol) in toluene (200 ml) was added over 10 minutes and the mixture was heated to 80°-85° C. After 16 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 yellow solid was stirred with ethyl acetate and filtered. The pale yellow solid (9.8 g, 57%) was used in the next reaction without further purification: m.p. (DSC) 182° C. Anal. Calc'd. for C12H12N2S2O2 : C, 51.41, H, 4.31, N, 9.99, S, 22.87 Found C, 51.02, H, 4.37, N, 9.80, S, 22.93,

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