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Method for preparing 2-alkyl benzimidazole compound

A technology of alkylbenzimidazole and compound, which is applied in the field of chemical synthesis, can solve problems such as long time and high temperature, and achieve the effects of short reaction time, low reaction temperature and simple post-treatment

Active Publication Date: 2014-04-23
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation of 2-substituted benzimidazoles by this method often requires harsh conditions - strong acidic conditions, high temperature, long time, etc.

Method used

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  • Method for preparing 2-alkyl benzimidazole compound
  • Method for preparing 2-alkyl benzimidazole compound
  • Method for preparing 2-alkyl benzimidazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1) Add a mol o-phenylenediamine and b mol formic acid (R=H) to a dry mortar, grind for 5 min, let stand for 20 min, then grind for 10 min, stand for 30 min, and grind for 15 min at 20°C. Let stand for 40 minutes to mix the raw materials uniformly and react the raw materials, where a:b=1:1;

[0029] 2) Place the mortar in an oven to continue the reaction of the raw materials. First, react at 50°C for 30 minutes, then increase the temperature to 80°C, react at 80°C for 60 minutes, and finally increase the temperature to 100°C and react at 100°C for 90 minutes to obtain the reaction mixture;

[0030] 3) Cool the reaction mixture to room temperature to obtain a suspension, adjust the pH of the suspension to 8.5 with a 5% mass concentration NaOH solution, and then wash it with water (directly add water to the pH-adjusted suspension ), suction filtration, the obtained filter cake is the crude product, and the crude product is recrystallized with absolute ethanol to obtain benzimi...

Embodiment 2

[0034] 1) Add a mol o-phenylenediamine and b mol acetic acid to a dry mortar (R=CH 3 ), at 25℃, first grind for 6min, stand for 15min, then grind for 10min, stand for 28min, finally grind for 18min, stand for 38min, make the raw materials mix uniformly, and make the raw materials react, where a:b=1:1 ;

[0035] 2) Place the mortar in an oven to continue the reaction of the raw materials, first react at 48°C for 35 minutes, then increase the temperature to 80°C, react at 80°C for 60 minutes, and finally increase the temperature to 100°C and react at 100°C for 90 minutes to obtain the reaction mixture;

[0036] 3) Cool the reaction mixture to room temperature to obtain a suspension, adjust the pH of the suspension to 8 with a 4% NaOH solution by mass concentration, then wash it with water and filter with suction. The obtained filter cake is the crude product. The crude product is recrystallized with absolute ethanol to obtain 2-methylbenzimidazole with a yield of over 90%. The struc...

Embodiment 3

[0040] 1) Add a mol o-phenylenediamine and b mol propionic acid to a dry mortar (R=C 2 H 5 ), at 22°C, first grind for 4 min, let stand for 18 min, then grind for 8 min, let stand for 26 min, and finally grind for 20 min, let stand for 35 min, so that the raw materials are mixed uniformly, and the raw materials are reacted, where a:b=1:1 ;

[0041] 2) Place the mortar in an oven to continue the reaction of the raw materials, first react at 52°C for 25 minutes, then increase the temperature to 78°C, react at 78°C for 55 minutes, and finally increase the temperature to 98°C and react at 98°C for 95 minutes to obtain a reaction mixture;

[0042] 3) Cool the reaction mixture to room temperature to obtain a suspension. Use a 3% NaOH solution to adjust the pH of the suspension to 9, then wash it with water and filter with suction. The resulting filter cake is the crude product. The crude product is recrystallized with absolute ethanol to obtain 2-ethylbenzimidazole with a yield of over ...

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Abstract

The invention provides a method for preparing a 2-alkyl benzimidazole compound. The preparation method comprises the steps of adding a mole of o-phenylenediamine and b mole of aliphatic carboxylic acid into a dry reaction container, evenly mixing raw materials and standing to react the raw materials to react, wherein a ratio of a to b is 1:(1-1.2); then placing the reaction container at a temperature of 45-100 DEG C to further react the raw materials, thereby obtaining a reaction mixture; cooling the reaction mixture to room temperature to obtain a suspension, adjusting a pH value of the suspension at 8-9, then scrubbing through water and filtering to obtain a filter cake which is a coarse product, and re-crystallizing the coarse product to obtain the 2-alkyl benzimidazole compound. The method is simple in experimental operation, cheap and available in raw materials, simple in experiment device, short in reaction time, low in reaction temperature, simple in postprocessing, high in yield of target product, and is environmental friendly; the method meets the requirements of industrial production; the method is an economical, simple and environment-friendly method for synthesizing the 2-alkyl benzimidazole compound.

Description

Technical field [0001] The invention belongs to the field of chemical synthesis, and particularly relates to a method for preparing 2-alkylbenzimidazole compounds. Background technique [0002] Benzimidazole compounds are an important pesticide and pharmaceutical intermediate. Because of their special structure, physiological activity and reactivity, they have a wide range of applications. The synthesis of such compounds, especially the synthesis of 2-position substituted benzimidazole derivatives, has attracted more and more attention. The existing method for preparing 2-substituted benzimidazole is to react o-phenylenediamine and carboxylic acid in a solvent. The preparation of 2-substituted benzimidazoles by this method often requires harsher conditions-strong acidic conditions, higher temperatures, and a long time. Today, when green chemistry is advocated, how to make the synthesis of benzimidazole compounds greener is still an important topic. Summary of the invention [0...

Claims

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Application Information

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IPC IPC(8): C07D235/06C07D235/08C07D235/14C07D235/10C07D235/12
CPCC07D235/06C07D235/08C07D235/10C07D235/12C07D235/14
Inventor 刘玉婷张晓莉刘蓓蓓靖春燕王捷梁钢涛尹大伟吕博
Owner SHAANXI UNIV OF SCI & TECH
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