반응 #79145

반응 방정식

(E)-cinnamoyl chloride

N-(3-pyridyl)-o-phenylenediamine

→

brown solids

수율 34.0%

(E)-1-(3-Pyridyl)-2-styryl-1H-benzimidazole

수율 34.0%

용매

xylene

반응 조건

후처리

1. 1
   온도the resulting mixture was heated
2. 2
   온도to reflux
3. 3
   기타removing water using a Dean-Stark apparatus for 11 h
4. 4
   온도After cooling
5. 5
   농축the reaction mixture was concentrated to dryness
6. 6
   workup.DISSOLUTIONThe residue was dissolved into ethyl acetate (100 ml)
7. 7
   세척washed consecutively with saturated aqueous sodium bicarbonate solution (50 ml) and brine (50 ml)
8. 8
   건조dried (magnesium sulfate)
9. 9
   농축concentrated to dryness
10. 10
    기타The residue was purified by column chromatography (silica gel, 165 g; n-hexane/ethyl acetate (3/2 to 1/1))

실험 절차

To a stirred suspension of N-(3-pyridyl)-o-phenylenediamine (0.93 g, 5 mmol; Kirsch, P.; Schoenleben-Janas, A.; Schirmer, R. H. Liebigs Ann. Org. Bioorg. Chem., 1995, 7, 1275) in xylene (60 ml) was added (E)-cinnamoyl chloride (0.83 g, 5 mmol). After stirring at the room temperature for 1h, the resulting mixture was heated to reflux removing water using a Dean-Stark apparatus for 11 h. After cooling, the reaction mixture was concentrated to dryness. The residue was dissolved into ethyl acetate (100 ml), washed consecutively with saturated aqueous sodium bicarbonate solution (50 ml) and brine (50 ml), dried (magnesium sulfate) and concentrated to dryness. The residue was purified by column chromatography (silica gel, 165 g; n-hexane/ethyl acetate (3/2 to 1/1)) to give 0.77 g (34%) of brown solids. Recrystallization from isopropyl ether yielded 0.50 g of the titled compound as pink solids. MW: 297.36; mp: 118.0-118.5° C.; 1H-NMR (CDCl3) δ: 8.84 (1H, dd, J=4.8, 1.5 Hz), 8.79 (1H, d, J=2.6 Hz), 8.00 (1H, d, J=15.8 Hz), 7.88-7.79 (2H, m), 7.61 (1H dd, J=8.1, 4.8 Hz), 7.50-7.44 (2H, m), 7.39-7.15 (6H, m), 6.78 (1H, d, J=15.8 Hz).

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