Preparation method for 1,2,4,5-tetra-substituted imidazole derivatives and catalyst for preparation

A technology of imidazole derivatives and four substitutions, which is applied in the field of ionic liquid catalysis, can solve the problems of complex product purification process, low raw material utilization rate, and difficult biodegradation, so as to reduce side reactions and impurities, improve utilization rate, and Good biodegradability effect

Active Publication Date: 2016-12-21
东港智科产业园有限公司
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0009] The purpose of the present invention is to overcome the high price of ionic liquid catalyst preparation, difficult biodegradation, low raw material utilization rate and high reaction temperature when ionic liquid is used to catalyze the preparation of 1,2,4,5-tetrasubstituted imidazole derivatives in the prior art , the product purification process is complicated and the catalyst needs to be processed before recycling, etc., a preparation method of 1,2,4,5-tetrasubstituted imidazole derivatives and a catalyst for its preparation are provided

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  • Preparation method for 1,2,4,5-tetra-substituted imidazole derivatives and catalyst for preparation
  • Preparation method for 1,2,4,5-tetra-substituted imidazole derivatives and catalyst for preparation
  • Preparation method for 1,2,4,5-tetra-substituted imidazole derivatives and catalyst for preparation

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preparation example Construction

[0042] The concrete steps of the preparation method of 1,2,4,5-tetrasubstituted imidazole derivatives of the present invention are:

[0043] (1) Weighing of raw materials: Accurately weigh the reaction raw materials benzil, aromatic aldehyde, aromatic amine and ammonium acetate according to the molar ratio of 1:1:1:(1-1.2).

[0044] (2) Catalyzed preparation: add the weighed reaction raw materials into the ethanol aqueous solution respectively, after fully dissolving and mixing uniformly, continue to add the acidic ionic liquid catalyst with benzil molar amount of 7-12% therein, and carry out under stirring conditions Heating to reflux reaction to obtain a solid precipitate, the volume of the above-mentioned aqueous ethanol solution in milliliters is 6 to 8 times the molar amount of benzil in millimoles, and the volume percent concentration of ethanol contained in the aqueous ethanol solution is 95 to 97 %, and the reaction pressure of the reflux reaction is an atmospheric pre...

Embodiment 1

[0052] 1mmol benzil, 1mmol p-chlorobenzaldehyde, 1mmol p-chloroaniline, 1mmol ammonium acetate and 0.08mmol ionic liquid catalyst were added to 8ml 97% ethanol aqueous solution in a 50ml single-necked bottle with a stirring bar and a condenser. Heat to reflux for 15 minutes, TLC (thin plate chromatography) detection, the raw material point disappears, cool to room temperature, crush the precipitated solid, let it stand, filter with suction, wash the filter residue with 97% ethanol aqueous solution, and vacuum dry to obtain 1,2-bis (4-Chlorophenyl)-4,5-diphenyl-1H-imidazole, the yield is 96%, directly add benzil, p-chlorobenzaldehyde, p-chloroaniline and ammonium acetate in the collected filtrate and repeat use.

[0053] 1,2-bis(4-chlorophenyl)-4,5-diphenyl-1H-imidazole obtained in this example: m.p.187~189°C; IR(KBr):1597, 1495, 1409cm -1 ; 1 H NMR (300MHz, DMSO-d 6 ): δ=6.89~7.65 (m, 18H, ArH)

Embodiment 2

[0055] 1mmol benzil, 1mmol benzaldehyde, 1mmol benzylamine, 1.2mmol ammonium acetate and 0.10mmol ionic liquid were respectively added to 6ml 97% ethanol aqueous solution in a 50ml single-necked bottle with a stirring bar and a condenser tube. Heat to reflux for 32 minutes, TLC (thin plate chromatography) detection, the raw material point disappears, cool to room temperature, crush the precipitated solid, let stand, filter with suction, the filter residue is washed with 97% ethanol aqueous solution, and vacuum dried to obtain 1-benzyl -4,5-diphenyl-2-phenyl-1H-imidazole, the yield is 88%. The collected filtrate is directly added with benzil, benzaldehyde, benzylamine and ammonium acetate for repeated use.

[0056] The performance parameters of 1-benzyl-4,5-diphenyl-2-phenyl-1H-imidazole obtained in this example are as follows: m.p.163~165°C; IR (KBr): 1596, 1493, 1471, 1412cm -1 ; 1 H NMR (300MHz, DMSO-d 6 ): δ=5.07(s, 2H, CH 2 ), 6.69-7.60 (m, 20H, ArH).

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Abstract

The invention discloses a preparation method for 1,2,4,5-tetra-substituted imidazole derivatives and a catalyst for preparation, and belongs to the technical field of ionic liquid catalysis. In a preparation reaction, the molar ratio of benzil to aromatic aldehyde to aromatic amine to ammonium acetate is 1 to 1 to 1 to (1-1.2), the molar amount of the ionic liquid catalyst is 7-12% of the used benzil molar amount, the volume amount of a reaction solvent ethanol aqueous solution in milliliter is 6-8 times of the molar amount of the benzil in millimole; the reflux reaction time is 15-45 min, cooling is performed to room temperature after the reaction is finished, suction filtration is performed, the filter residue is washed with the ethanol aqueous solution and subjected to vacuum drying to obtain the 1,2,4,5-tetra-substituted imidazole derivatives. The preparation method has the advantages of high catalyst activity, biodegradability, simple product purification, high raw material utilization rate, simple and convenient operation in the whole preparation process and the like, and is convenient for large-scale industrialized application.

Description

technical field [0001] The invention belongs to the technical field of ionic liquid catalysis, and more specifically relates to a preparation method of 1,2,4,5-tetrasubstituted imidazole derivatives and a high-acidity ionic liquid catalyst for the preparation thereof. Background technique [0002] Imidazole is an important class of nitrogen-containing five-membered heterocyclic compounds. Its importance lies not in its monomers, but in its derivatives with various substituents. Polysubstituted imidazoles mainly include trisubstituted imidazoles and tetrasubstituted imidazoles, most of which have strong physiological properties, such as antifungal, antiapoptotic, antiviral, anti-inflammatory, antitumor and other activities, and are widely used in medical and agricultural fields. In addition, multi-substituted imidazole compounds, especially tetra-substituted imidazole derivatives also have excellent optical properties, so they are widely used in the fields of fluorescence, im...

Claims

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Application Information

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IPC IPC(8): B01J31/02C07C305/04C07D233/64C07D233/58
CPCB01J31/0279C07C305/04C07D233/58C07D233/64
Inventor 沈智培卢华沈建忠
Owner 东港智科产业园有限公司
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