Method for preparing 2,4,5-triaryl substituted imidazole through catalysis of degradable acidic ionic liquid

A technology for the preparation of acidic ionic liquids and catalysis, applied in organic chemistry, etc., can solve the problems of large amount of ionic liquids used, difficult to biodegrade, and high preparation costs, and achieve the effect of less catalysts used, cheap raw materials, and simple preparation process

Active Publication Date: 2014-06-25
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome the ionic liquids in the process of preparing 2,4,5-triaryl-substituted imidazoles in the prior art by using acidic ionic liquids to catalyze the preparation of 2,4,5-triaryl-substituted imidazoles. The amount of loss is also relatively large and other shortcomings, and a kind of easy biodegradation, high acidity, simple preparation and low price Bronster acidic ionic liquid is provided as a green catalyst, which can be used to catalyze the preparation of 2,4,5-triaryl under solvent-free conditions. Method of replacing imidazole

Method used

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  • Method for preparing 2,4,5-triaryl substituted imidazole through catalysis of degradable acidic ionic liquid
  • Method for preparing 2,4,5-triaryl substituted imidazole through catalysis of degradable acidic ionic liquid
  • Method for preparing 2,4,5-triaryl substituted imidazole through catalysis of degradable acidic ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: 5mmol benzaldehyde, 5mmol benzil, 10mmol ammonium acetate and 0.15mmol degradable acidic ionic liquid were respectively added to 50ml single-necked bottles containing 5ml ethanol with a stirring bar and a condenser tube. Reflux reaction for 1.2h under vigorous stirring, TLC (thin plate chromatography, developer is V (ethyl acetate): V (petroleum ether) = 1:3) detection, the raw material point disappeared, distilled ethanol by rotary evaporator, added 15ml A large amount of solids precipitated after watering, crushed the solids, stood still, and filtered with suction. The resulting filter residue was washed with water, dried, and then recrystallized with ethanol. After vacuum drying, pure 2,4,5-triphenylimidazole was obtained with a yield of 95%. After the filtrate was evaporated to remove water, the reaction raw materials and ethanol were directly added for repeated use.

[0023] 2,4,5-Triphenylimidazole: m.p.269°C; 1 H NMR (400MHz, DMSO-d 6 ): δ=7.17~8.05(...

Embodiment 2

[0024] Example 2: 5mmol p-chlorobenzaldehyde, 5mmol benzil, 10mmol ammonium acetate and 0.20mmol degradable acidic ionic liquid were added to 50ml single-necked bottles containing 10ml ethanol with a stirring bar and a condenser. Reflux reaction for 1.5h under vigorous stirring, TLC (thin plate chromatography, developer is V (ethyl acetate): V (petroleum ether) = 1:3) detection, the raw material point disappeared, distilled ethanol by rotary evaporator, added 15ml A large amount of solids precipitated after watering, crushed the solids, stood still, filtered with suction, washed the obtained filter residue with water, dried and recrystallized with ethanol, and obtained pure 2-(4'-chlorophenyl)-4,5-diphenyl Kiimidazole, the yield is 81%. After the filtrate was evaporated to remove water, the reaction raw materials and ethanol were directly added for repeated use.

[0025] 2-(4'-chlorophenyl)-4,5-diphenylimidazole: m.p.266~268℃; 1 H NMR (400MHz, DMSO-d 6 ): δ=7.14~8.01(m, 14H...

Embodiment 3

[0026] Example 3: 5mmol o-chlorobenzaldehyde, 5mmol benzil, 10mmol ammonium acetate and 0.20mmol degradable acidic ionic liquid were added to 10ml ethanol in a 50ml single-necked bottle with a stirring bar and a condenser. Reflux reaction for 2 hours under vigorous stirring, TLC (thin plate chromatography, developer is V (ethyl acetate): V (petroleum ether) = 1:3) detection, the raw material point disappeared, distilled ethanol by rotary evaporator, added 15ml of water Afterwards, a large amount of solids precipitated, crushed the solids, stood still, and filtered with suction. The resulting filter residue was washed with water, dried, and then recrystallized with ethanol. After vacuum drying, pure 2-(2'-chlorophenyl)-4,5-diphenyl Imidazole, the yield is 78%. After the filtrate was evaporated to remove water, the reaction raw materials and ethanol were directly added for reuse.

[0027]2-(2'-chlorophenyl)-4,5-diphenylimidazole: m.p.196~198℃; 1 H NMR (400MHz, DMSO-d 6 ): δ=7...

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Abstract

The invention discloses a method for preparing 2,4,5-triaryl substituted imidazole through catalysis of a degradable acidic ionic liquid, belonging to the technical field of preparation of chemical materials. According to the preparation method, a mol ratio of dibenzoyl to aromatic aldehyde to ammonium acetate is 1:1:(2-4), the molar weight of a degradable acidic ionic liquid catalyst accounts for 3-5 percent of that of the used aromatic aldehyde, and the volume (ml) of alcohol as a reaction solvent is 1-3 times molar weight (mmol) of that of the aromatic aldehyde. The method comprises the steps: performing a reflux reaction for 0.5-2 hours, rotatably evaporating a solvent after the reaction is ended, separating out a large quantity of solids after adding water, grinding solids, standing, carrying out suction filtering, washing filter residue, recrystalizing by using alcohol after drying, and drying in vacuum to obtain 2,4,5-triaryl substituted imidazole. Compared with a preparation method of other acidic ionic liquid catalysts, the method has the advantages of good activity of the catalyst, simplicity, convenience and low cost in the whole preparation process, and the like, and is easy to degrade, and brings the convenience to industrialized large-scale production.

Description

technical field [0001] The invention belongs to the technical field of chemical material preparation, and in particular relates to a method for catalytically preparing 2,4,5-triaryl-substituted imidazoles by a degradable acidic ionic liquid. The method is suitable for the occasion of catalyzing the preparation of 2,4,5-triaryl-substituted imidazoles with aromatic aldehydes, benzyl and ammonium acetate as raw materials. Background technique [0002] Imidazole is very close to the composition of organisms in structure and composition, and is also the active group of many important biological functional molecules. It is mainly used in the fields of medicine and biology, and has a broad application space in organic synthesis intermediates. At the same time, imidazoles Compounds also have broad applications in the fields of surfactants, analysis, and chemical engineering. In addition, the aryl-substituted imidazole derivatives have anti-inflammatory, anti-tumor and other physiol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64
CPCC07D233/58C07D233/64
Inventor 岳彩波高学频吴胜华诸荣孙
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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