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Method for synthesizing benzimidazole compounds

A technology for benzimidazoles and compounds is applied in the field of one-step synthesis of benzimidazole compounds, which can solve the problems of troublesome product separation and many reaction steps, achieve convenient product separation, reduce the generation of by-products, and avoid strong oxidants and strong acid solvents. the effect of using

Inactive Publication Date: 2013-09-11
海宁市盐官工业投资有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Not only the reaction steps are many, but also the product separation of some reactions is troublesome

Method used

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  • Method for synthesizing benzimidazole compounds
  • Method for synthesizing benzimidazole compounds
  • Method for synthesizing benzimidazole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Take 10g Al 2 o 3 Add water and stir, heat in a water bath to 80°C, add 10mL of H 2 PdCl 4 solution (Pd content is 0.03g / mL), 10mL Zn(NO 3 ) 2 solution (Zn content is 0.02g / mL) and 10mL Cu(NO 3 ) 2 solution (Cu content is 0.04g / mL), kept at 80°C for 5 hours, then added dropwise NH 4 HCO 3 Adjust the pH value of the solution to 8-10, keep the solution temperature and stir for 1 hour; filter, wash the filter cake with deionized water until neutral; vacuum dry at 110°C for 4 hours; then, roast at 260°C for 4 hours, and finally in Reduction with hydrogen at 260°C for 4 hours, that is, Cu4wt%-Zn2wt%-Pd3wt% / Al with the corresponding loading amount can be obtained 2 o 3 catalyst.

Embodiment 2

[0032] Take 10g Al 2 o 3 Add water and stir, heat in a water bath to 80°C, add dropwise 20mL of Pd(NO 3 ) 2 solution (Pd content is 0.01g / mL), 5mL ZnCl 2 solution (Zn content is 0.02g / mL) and 5mL CuCl 2 solution (Cu content is 0.1g / mL), kept at 70°C for 3 hours, then added dropwise (NH 4 ) 2 CO 3 Adjust the pH value of the solution to 8-10, keep the solution temperature and stir for 4 hours; filter, wash the filter cake with deionized water until neutral; vacuum dry at 90°C for 6h; then, roast at 360°C for 5h, and finally in Reduction with hydrogen at 300°C for 3 hours, that is, Cu5wt%-Zn1wt%-Pd2wt% / Al with corresponding loads 2 o 3 catalyst.

Embodiment 3

[0034] Take 10g Al 2 o 3 Add water and stir, heat in a water bath to 80°C, add dropwise 30mL of Pd(C 2 h 3 o 2 ) 2 solution (Pd content is 0.01g / mL), 5mL Zn(NO 3 ) 2 solution (Zn content is 0.01g / mL) and 10mL Cu(NO 3 ) 2 solution (Cu content is 0.02g / mL), kept at 90°C for 8 hours, added dropwise NaOH solution to adjust the pH value to 8-10, kept the solution temperature and stirred for 2 hours; filtered, and the filter cake was washed with deionized water until medium properties; vacuum drying at 100°C for 8h; then calcination at 400°C for 5h, and finally, hydrogen reduction at 350°C for 3h to obtain Cu2wt%-Zn0.5wt%-Pd3wt% / Al 2 o 3 catalyst.

[0035] Embodiment 4 to Embodiment 12 are Cu-Zn-Pd / Al prepared by the above method 2 o 3 Examples of catalysts used in the synthesis of benzimidazoles:

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Abstract

The invention discloses a method for synthesizing benzimidazole compounds expressed by a formula (III) through a one-pot method. The method comprises the following step of: with ortho-nitroaniline compounds expressed by a formula (I) and fatty alcohol expressed by a formula (II) as raw materials as well as water as a reaction solvent, synthesizing the benzimidazole compounds expressed by the formula (III) through the one-pot method in a shielding gas atmosphere under the action of a supported metal solid catalyst, wherein the supported metal solid catalyst is a Cu-Zn-Pd / Al2O3 catalyst. The method disclosed by the invention has the advantages of being simple in synthesis route, high in product yield, low in production cost, liable to separate the selected solid catalyst, high in activity, good in stability and free of liquid acid and organic solvent, and the like, thereby being an environment-friendly synthesis route. FORMUAL (I), R1CH2OH (II), (III) are described in the specification.

Description

technical field [0001] The invention relates to a method for synthesizing benzimidazole compounds in one step by using o-nitroaniline compounds and fatty alcohols as raw materials. Background technique [0002] Benzimidazole or substituted benzimidazole is an important organic drug synthesis intermediate, which has a wide range of biological and physiological activities, such as antifungal, antiviral, anticancer, antitumor, blood pressure lowering and hypoglycemic effects; and transition The complexes formed by metal ions can be used to simulate the biological activity of natural superoxide dismutase (SOD); they can also be used as new curing agents for epoxy resins, surface treatment agents or catalysts for metals, etc. Therefore, the synthesis of benzimidazoles or substituted benzimidazoles has attracted much attention. [0003] Under the action of an acidic catalyst, using o-phenylenediamine and aldehydes, carboxylic acids, ester derivatives, etc. as raw materials, dehyd...

Claims

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Application Information

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IPC IPC(8): C07D235/06C07D235/08B01J23/89
Inventor 李小年叶佳张群峰卢春山丰枫许孝良马磊
Owner 海宁市盐官工业投资有限公司
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