A kind of 2-aryl-1,3-dihydrobenzimidazole derivative and its synthesis method and application
A synthetic method and compound technology, applied in the field of medicine, can solve the problems that have not been seen before, and achieve good medicinal value and remarkable effect of anti-renal fibrosis activity
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Embodiment 1
[0023] 1) Add 1.53g (10mmol) of 4-nitro-o-phenylenediamine, 1.75g (10mmol) of 2,4-dichlorobenzaldehyde, and 50ml of anhydrous methanol into a 150ml round bottom flask, heat to reflux temperature for 8h . After the reaction was completed, it was cooled to room temperature, and the orange crude product was obtained by suction filtration.
[0024] 2) The crude product was subjected to silica gel column chromatography using a solvent composed of petroleum ether:dichloromethane=100:20 (volume ratio) as an eluent to obtain an orange solid product (2.85 g, yield 92%).
[0025] The resulting orange solid product is characterized by nuclear magnetic resonance, and its proton nuclear magnetic resonance spectrum and carbon spectrum are respectively as follows figure 1 with 2 shown.
[0026] 1 H NMR (500MHz, DMSO-d6) δ8.96(s, 1H), 8.45(d, J=8.5Hz, 1H), 8.00(d, J=2.5Hz, 1H), 7.95(dd, J=9.0, 2.5Hz, 1H), 7.77(d, J=2.0Hz, 1H), 7.57(dd, J=8.5, 1.7Hz, 1H), 6.85(s, 2H), 6.79(d, J=9.0Hz, 1...
Embodiment 2
[0030] 1) Add 1.53g (10mmol) of 4-nitro-o-phenylenediamine, 0.88g (5mmol) of 2,4-dichlorobenzaldehyde, and 50ml of absolute ethanol into a 150ml round bottom flask, heat to reflux temperature and reflux for 8h . After the reaction was completed, it was cooled to room temperature, and the orange crude product was obtained by suction filtration.
[0031] 2) The crude product was subjected to column chromatography using a solvent composed of petroleum ether:dichloromethane=100:15 (volume ratio) as an eluent to obtain an orange solid product (1.36 g, yield 88%).
[0032] The obtained orange solid product was identified as 2-(2,4-dichlorophenyl)-5-nitro-1,3-dihydrobenzimidazole according to the present invention through NMR characterization.
Embodiment 3
[0034] 1) Add 1.53g (10mmol) of 4-nitro-o-phenylenediamine, 1.75g (10mmol) of 2,4-dichlorobenzaldehyde, 25ml of methanol and 25ml of absolute ethanol into a 150ml round bottom flask and heat to Reflux temperature reflux reaction 6h. After the reaction was completed, it was cooled to room temperature, and the orange crude product was obtained by suction filtration.
[0035] 2) The crude product was subjected to column chromatography with a solvent composed of petroleum ether:dichloromethane=100:15 (volume ratio) as an eluent, and an orange solid product (2.48 g, yield 80%) was obtained.
[0036] The obtained orange solid product was identified as 2-(2,4-dichlorophenyl)-5-nitro-1,3-dihydrobenzimidazole according to the present invention through NMR characterization.
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