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Copper-catalyzed N-alkylated benzimidazole derivative and complex one-step in-situ synthesis method

A technology for the synthesis of benzimidazole and its synthesis method, which is applied in the field of synthesis of copper-catalyzed N-alkylated benzimidazole derivatives and complexes, can solve the problems of high cost, long reaction time, separation, etc., and achieve easy control and condition Gentle, easy-to-synthesize effects

Inactive Publication Date: 2021-03-26
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that the reaction time is long, the raw materials and solvents used pollute the environment, bring the trouble of harmless treatment, and require product separation process, etc.; second, two raw materials of halogenated alkanes and benzimidazole derivatives are required; or two reactions are required Raw materials or two or more reaction raw materials (such as aromatic aldehydes and aromatic diamine compounds) to produce another kind of N-alkylated benzimidazole derivatives, often accompanied by by-products, need to be separated; third, some new Synthesis methods require surfactants, ionic liquids, or microwave-assisted synthesis, etc., which are expensive and require instrument assistance

Method used

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  • Copper-catalyzed N-alkylated benzimidazole derivative and complex one-step in-situ synthesis method
  • Copper-catalyzed N-alkylated benzimidazole derivative and complex one-step in-situ synthesis method
  • Copper-catalyzed N-alkylated benzimidazole derivative and complex one-step in-situ synthesis method

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Experimental program
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Embodiment 1

[0024] 0.2mmol catalyst CuCl 2 , 0.2mmol raw material 2-phenylbenzimidazole-5-sulfonic acid was dissolved in 10mL deionized water, added 0.2mmol NaOH and stirred at room temperature for 2h, then, 0.2mmol 2,2′-bipyridine in 10mL ethanol solution was added to the above The solution was heated to reflux at 80°C for 12h, and cooled to room temperature. It was filtered and placed at room temperature, and blue blocky crystals were obtained after 7d.

Embodiment 2

[0026] 0.3mmol catalyst CuCl 2 , 0.3mmol raw material 2-phenylbenzimidazole-5-sulfonic acid was dissolved in 10mL deionized water, added 0.3mmol NaOH and stirred at room temperature for 2h, then, 0.3mmol 2,2'-bipyridine in 10mL ethanol solution was added to the above The solution was heated to reflux at 80°C for 12h, and cooled to room temperature. It was filtered and placed at room temperature, and blue blocky crystals were obtained after 7d.

Embodiment 3

[0028] 0.4mmol catalyst CuCl 2 , 0.4mmol raw material 2-phenylbenzimidazole-5-sulfonic acid was dissolved in 10mL deionized water, added 0.4mmol NaOH and stirred at room temperature for 2h, then, 0.4mmol 2,2′-bipyridine in 10mL ethanol solution was added to the above The solution was heated to reflux at 80°C for 12h, and cooled to room temperature. It was filtered and placed at room temperature, and blue blocky crystals were obtained after 7d.

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Abstract

The invention relates to the field of organic synthesis and optics, in particular to a synthesis method of copper catalyzed N-alkylated benzimidazole derivatives and complexes. The method comprises the following steps: dissolving 0.1 mmol of catalyst CuCl2 and 0.1 mmol of raw material 2-phenyl benzimidazole 5sulfonic acid into 10mL of deionized water, adding 0.1 mmol of NaOH, stirring at room temperature for 2 hours, adding 0.1 mmol of 10mL of ethanol solution of 2, 2 '-dipyridyl into the solution, heating and refluxing at 80 DEG C for 12 hours, cooling to room temperature, filtering and standing at room temperature for 7 days to obtain blue blocky crystals. Compared with the prior art, the preparation method has the following advantages that CuCl2 is used as a catalyst, 2-phenylbenzimidazole 5-sulfonic acid is used as a raw material, and N-benzyl 2-phenylbenzimidazole 5-sulfonic acid and the copper complex thereof are obtained through one-step synthesis in a water and ethanol system.Two raw materials of 2phenyl benzimidazole 5sulfonic acid and benzyl halide are not used. One reactant raw material is used, a target product and a complex of the target product are synthesized through a one-step in-situ synthesis reaction, and an organic solvent which pollutes the environment and needs harmless treatment is not used. Other auxiliary equipment is not needed. The synthesis method is simple, and experimental conditions are mild.

Description

technical field [0001] The invention relates to the fields of organic synthesis and optics, in particular to a method for synthesizing copper-catalyzed N-alkylated benzimidazole derivatives and complexes. Background technique [0002] There are many methods for synthesizing N-alkylated benzimidazole derivatives in the prior art. First, conventional synthesis requires the use of alkyl halides as raw materials, organic solvents such as DMF and DMSO. The disadvantage is that the reaction time is long, the raw materials and solvents used pollute the environment, bring the trouble of harmless treatment, and require product separation process, etc.; second, two raw materials of halogenated alkanes and benzimidazole derivatives are required; or two reactions are required Raw materials or two or more reaction raw materials (such as aromatic aldehydes and aromatic diamine compounds) to produce another kind of N-alkylated benzimidazole derivatives, often accompanied by by-products, n...

Claims

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Application Information

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IPC IPC(8): C07F1/08C09K11/06
CPCC07F1/005C09K11/06C07B2200/13C09K2211/188
Inventor 王莹关磊
Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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