반응 #62216

반응 방정식

4-Methoxyaniline

pyridine-4-carboxaldehyde

potassium carbonate

tosylmethylisocyanide

→

title compound

수율 56.0%

4-(1-(4-methoxyphenyl)-1H-imidazol-5-yl)pyridine

수율 56.0%

용매

methanol

1,2-dimethoxyethane

toluene

반응 조건

후처리

1. 1
   온도reflux condensor
2. 2
   온도was heated
3. 3
   온도at reflux
4. 4
   기타The toluene was removed via distillation through the Dean-Stark sidearm
5. 5
   workup.DISSOLUTIONthe residue was dissolved in methanol (100 mL)
6. 6
   온도was heated
7. 7
   온도at reflux for 3 hours
8. 8
   기타the solvent was removed in vacuo
9. 9
   workup.DISSOLUTIONthe residue was dissolved in methylene chloride
10. 10
    세척was washed with brine
11. 11
    추출The brine layer was extracted with methylene chloride
12. 12
    건조the combined organic layers were dried (MgSO4)
13. 13
    여과were filtered
14. 14
    농축were concentrated in vacuo
15. 15
    기타The residue was purified by silica gel chromatography with ethyl acetate—hexanes—methanol (80:20:0 to 76:19:5)

실험 절차

4-Methoxyaniline (2.46 g, 20 mmol) and pyridine-4-carboxaldehyde (1.9 mL, 10 mmol) in toluene (110 mL) in a flask attached to a Dean-Stark trap and reflux condensor was heated at reflux. After 40 hours, the reaction was complete by infrared spectral analysis and mass spectral analysis. The toluene was removed via distillation through the Dean-Stark sidearm, the residue was dissolved in methanol (100 mL) and ca. ½ of the crude imine (ca. 10 mmol, 50 mL of methanol solution) was diluted with methanol (20 mL) and 1,2-dimethoxyethane (20 mL). The solution was then treated with potassium carbonate (2.76 g, 20 mmol) and tosylmethylisocyanide (TOSMIC, 2.93 g, 15 mmol) and was heated at reflux for 3 hours. After cooling to room temperature, the solvent was removed in vacuo, and the residue was dissolved in methylene chloride and was washed with brine. The brine layer was extracted with methylene chloride and the combined organic layers were dried (MgSO4), were filtered, and were concentrated in vacuo. The residue was purified by silica gel chromatography with ethyl acetate—hexanes—methanol (80:20:0 to 76:19:5) to afford 1.4 g (56% yield) of the title compound; diagnostic 13C NMR signals (100 MHz, CDCl3) δ 160.039, 150.161, 141.009, 137.240, 130.839, 129.179, 127.287, 121.597, 115.106, 55.801; MS (AP/Cl) 252.4 (M+H)+.

출처