반응 #804510

반응 방정식

4-methyl-N-phenylbenzamide

PCl5

2-ethoxy-2-oxoacetonitrile

SnCl4

→

ethyl 2-(4-methylphenyl)quinazoline-4-carboxylate

용매

toluene

반응 조건

후처리

1. 1
   기타Into a 100-mL 3-necked round-bottom flask purged
2. 2
   온도maintained with an inert atmosphere of nitrogen
3. 3
   농축The mixture was concentrated under vacuum
4. 4
   workup.ADDITIONThe residue was diluted with 30 mL of PhCl
5. 5
   기타to react
6. 6
   workup.STIRRINGwith stirring, overnight while the temperature
7. 7
   온도was maintained at 125° C. in an oil bath
8. 8
   농축The resulting mixture was concentrated under vacuum
9. 9
   추출The residue was extracted with 3×100 mL of ethyl acetate
10. 10
    세척The resulting mixture was washed with 4×100 mL of water
11. 11
    건조The mixture was dried over anhydrous sodium sulfate
12. 12
    농축concentrated under vacuum
13. 13
    기타This resulted in 2.64 g (32%) of ethyl 2-(4-methylphenyl)quinazoline-4-carboxylate as a light green solid

실험 절차

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-methyl-N-phenylbenzamide (6 g, 28.40 mmol, 1.00 equiv) in toluene (60 mL) and PCl5 (7.13 g, 34.24 mmol, 1.20 equiv). The mixture was stirred for 2 h at 65° C. The mixture was concentrated under vacuum. The residue was diluted with 30 mL of PhCl. To the mixture was added 2-ethoxy-2-oxoacetonitrile (3.37 g, 34.01 mmol, 1.20 equiv), SnCl4 (12.5 g, 1.70 equiv). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 125° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was extracted with 3×100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 4×100 mL of water. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:30). This resulted in 2.64 g (32%) of ethyl 2-(4-methylphenyl)quinazoline-4-carboxylate as a light green solid. MS (ESI) m/z 293 ([M+H]+).

출처