반응 #79192

반응 방정식

2,3-diaminotoluene

(E)-cinnamic acid

sodium hydroxide

→

titled compound

수율 13.0%

(E)-4-Methyl-2-styryl-1H-benzimidazole

수율 13.0%

용매

water

반응 조건

후처리

1. 1
   추출extracted with dichloromethane (3×100 ml)
2. 2
   세척The combined extracts were washed with water (100 ml) and brine (100 ml)
3. 3
   건조dried (magnesium sulfate)
4. 4
   농축concentrated to dryness
5. 5
   기타Purification by column chromatography (silica gel, 300 g; n-hexane/ethyl acetate (7/3))

실험 절차

A mixture of 2,3-diaminotoluene (2.44 g, 20 mmol), (E)-cinnamic acid (2.96 g, 20 mmol) and polyphosphoric acid (10 g) was heated to 180° C. for 90 min. The hot mixture was poured into water (100 ml), basified with 50% aqueous solution of sodium hydroxide and extracted with dichloromethane (3×100 ml). The combined extracts were washed with water (100 ml) and brine (100 ml), dried (magnesium sulfate) and concentrated to dryness. Purification by column chromatography (silica gel, 300 g; n-hexane/ethyl acetate (7/3)) yielded 0.61 g (13%) of the titled compound as red solids. 1H-NMR (CDCl3) δ: 9.53 (1H, br.s), 8.72-8.67 (1H, m), 7.95 (1H ddd, J=7.7, 7.7, 1.8 Hz), 7.60-7.49 (3H, m), 7.43-7.31 (3H, m), 7.23-7.14 (3H, m), 7.09-7.04 (1H, m), 2.63 (3H, br.s)

출처