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Preparation method of 2-arylbenzimidazole

A technology of benzimidazole and aryl group, applied in the field of preparing 2-arylbenzimidazole, can solve the problems of complicated post-processing process, high catalyst cost, long reaction time and the like, and achieves short reaction time, good catalytic effect and low cost low effect

Inactive Publication Date: 2013-05-01
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method successfully synthesized the target product with a high yield, the cost of the catalyst used was high, the reaction time was long, the post-treatment process was complicated, and the synthesis process still needs to be further improved.

Method used

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  • Preparation method of 2-arylbenzimidazole
  • Preparation method of 2-arylbenzimidazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1) Add 0.01mol of o-phenylenediamine and 0.01mol of benzoic acid to a dry three-necked flask, then add 5mL of 1,4-dioxane, and then add 0.001mol of concentrated sulfuric acid with a mass concentration of 98% dropwise under stirring , kept at 102°C and refluxed for 5 hours under sufficient stirring to obtain a mixed solution;

[0023] 2) Cool the mixed solution to room temperature, then add NaOH aqueous solution with a mass concentration of 10% to the mixed solution to make the mixed solution alkaline and precipitate solids, then filter the mixed solution under reduced pressure, and air-dry the obtained solid naturally, that is 2-Phenylbenzimidazole was obtained in a yield of 76%.

[0024] The present invention further provides the comparative example of embodiment 1, promptly does not add the preparation method of concentrated sulfuric acid catalyst and prepares 2-phenylbenzimidazole, and its preparation method is as follows:

[0025] 1) Add 0.01mol of o-phenylenediami...

Embodiment 2

[0029] 1) Add 0.01mol of o-phenylenediamine and 0.011mol of benzoic acid to a dry three-necked flask, then add 5mL of 1,4-dioxane, and then add 0.001mol of concentrated sulfuric acid with a mass concentration of 98% dropwise under stirring , keep reflux at 102°C for 4.5h under sufficient stirring to obtain a mixed solution;

[0030] 2) Cool the mixed solution to room temperature, then add NaOH aqueous solution with a mass concentration of 10% to the mixed solution to make the mixed solution alkaline and precipitate solids, then filter the mixed solution under reduced pressure, and air-dry the obtained solid naturally, that is 2-Phenylbenzimidazole was obtained with a yield of 85%.

Embodiment 3

[0032] 1) Add 0.01mol of o-phenylenediamine and 0.012mol of benzoic acid to a dry three-necked flask, then add 5mL of 1,4-dioxane, and then add 0.001mol of concentrated sulfuric acid with a mass concentration of 98% dropwise under stirring , keep reflux at 102°C for 4h under sufficient stirring to obtain a mixed solution;

[0033] 2) Cool the mixed solution to room temperature, then add NaOH aqueous solution with a mass concentration of 10% to the mixed solution to make the mixed solution alkaline and precipitate solids, then filter the mixed solution under reduced pressure, and air-dry the obtained solid naturally, that is 2-Phenylbenzimidazole was obtained in 90% yield, IR(υ max , KBr, cm -1 ): 1625(-C=N), 3190(-NH); 1 HNMR (δppm, CDCl 3 ):12.96(s,1H,-NH),7.94(d,2H,Ar-H),7.25-7.27(m,4H,Ar-H),7.41-7.44(m,1H,Ar-H),6.90 -6.92 (m, 2H, Ar-H).

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Abstract

The invention provides a preparation method of 2-arylbenzimidazole, which comprises the steps of firstly adding ortho-phenylene diamine and benzoic acid or substituted benzoic acid into a reactor, then adding 1,4-dioxane, dropwise adding concentrated sulfuric acid while stirring, stirring for back flow for 3-5h, obtaining a mixed solution, cooling the mixed solution to the room temperature, adding a NaOH water solution into the mixed solution, allowing a solid to be precipitated in the mixed solution, conducting suction filtrationunder reduced pressure, drying, and obtaining 2-arylbenzimidazole. According to the method, 2-arylbenzimidazole is prepared by taking 1,4-dioxane as a solvent and concentrated sulfuric acid as a catalyst and adopting a one-pot method; concentrated sulfuric acid is cheap, easy to get and good in catalytic effect; therefore, the method is simple in operational process, low in cost, and short in reaction time. In addition, with the adoption of the method, as high yield of 2-arylbenzimidazole can be realized without recrystallization, the post-treatment is simple.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing 2-arylbenzimidazoles. Background technique [0002] Benzimidazoles are benzoheterocyclic compounds containing two nitrogen atoms. Benzimidazole and its derivatives have good biological activities (such as anticancer, antibacterial, antiparasitic, etc.), and can be used as drug intermediates, and some products have been used in clinical treatment. However, the existing varieties are constantly modified and improved. Research on structures to obtain new varieties with high activity and low toxicity has never been interrupted. In recent years, the synthesis and biological activity of benzimidazoles have increasingly become a hot spot in the research of heterocyclic chemistry. New compounds and new uses have been reported continuously, and related synthesis research has also attracted the attention of researchers. , people are trying to find a more efficient...

Claims

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Application Information

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IPC IPC(8): C07D235/18
Inventor 刘玉婷付青尹大伟蒋闪闪吕博李鑫
Owner SHAANXI UNIV OF SCI & TECH
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