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Method for preparing 2,6-bis(2-benzimidazolyl)pyridine

A technology of benzimidazolyl pyridine and benzimidazole, applied in the field of aromatic organic compounds, can solve the problems of harsh reaction conditions, complicated operation and high cost, and achieve the effects of easy separation and purification, simple operation and high yield

Inactive Publication Date: 2012-11-21
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The catalyst CuI used in the method and 1,3-bis(2-pyridine)-1,3-propanedione are expensive, the production cost is high, and column chromatography is used for separation and purification in the aftertreatment process, which is unfavorable for suitability for industrialized production
[0003] Obviously, there are problems such as complex operation, harsh reaction conditions, high cost, and difficult separation and purification of reactants in the above-mentioned method.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Equipped with magnetic stirrer, reflux condenser, thermometer, anhydrous CaCl 2 In the 100ml four-necked flask of the drying tube, add 1.18g (5mmol) 2,6-dibromopyridine, 1.30g (11mmol) benzimidazole, 0.32g (5mmol) copper powder, 0.69g (5mmol) anhydrous potassium carbonate , 0.28g (5mmol) potassium hydroxide and 50mL DMF, control the temperature at 130°C and react for 48h, then cool the reaction mixture to room temperature, add an appropriate amount of ammonia water, and stir for 30min. The reaction mixture was poured into a beaker filled with ice water, stirred, allowed to stand, filtered with suction, and dried to obtain a crude product. The crude product was recrystallized from ethanol to obtain 1.37 g of a white solid product with a yield of 88.4% and a purity of 98.7%.

Embodiment 2

[0014] Equipped with magnetic stirrer, reflux condenser, thermometer, anhydrous CaCl 2 In the 100ml four-necked flask of the drying tube, add 1.18g (5mmol) 2,6-dibromopyridine, 1.30g (11mmol) benzimidazole, 0.32g (5mmol) copper powder, 0.69g (5mmol) anhydrous potassium carbonate , 0.28g (5mmol) potassium hydroxide and 50mL DMF, heated to reflux for 48h to stop the reaction. Cool the reaction mixture to room temperature, add an appropriate amount of ammonia water, and stir for 30 min. The reaction mixture was poured into a beaker filled with ice water, stirred, allowed to stand, filtered with suction, and dried to obtain a crude product. The crude product was recrystallized from ethanol to obtain 1.41 g of a white solid product with a yield of 90.8% and a purity of 98.5%.

Embodiment 3

[0016] Equipped with magnetic stirrer, reflux condenser, thermometer, anhydrous CaCl 2 In the 100ml four-necked flask of the drying tube, add 1.18g (5mmol) 2,6-dibromopyridine, 1.30g (11mmol) benzimidazole, 0.38g (6mmol) copper powder, 0.83g (6mmol) anhydrous potassium carbonate , 0.34g (6mmol) potassium hydroxide and 50mL DMF, heated to reflux for 48h to stop the reaction. Cool the reaction mixture to room temperature, add an appropriate amount of ammonia water, and stir for 30 min. The reaction mixture was poured into a beaker filled with ice water, stirred, allowed to stand, filtered with suction, and dried to obtain a crude product. The crude product was recrystallized from ethanol to obtain 1.36 g of a white solid product with a yield of 87.7% and a purity of 98.3%.

[0017] Physical constants and spectral data of the product: Appearance: white solid; melting point: 226-228°C;

[0018] IR (KBr, cm -1 ):3112.89,3053.11,2923.88,2852.52,1782.10,1598.88,1581.52,1502.44,14...

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PUM

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Abstract

The invention provides a method for preparing 2,6-bis(2-benzimidazolyl)pyridine, which comprises the following steps: adding weighed 2,6-dibromopyridine, benzimidazole, potassium hydroxide, potassium carbonate and copper powder into a reactor, and reacting in presence of N,N-dimethylformamide serving as a solvent at a temperature between 100 DEG C and a refluxing temperature for 24 to 56 hours; and cooling, adding ammonia water, stirring, pouring reactants into ice water, standing, filtering under vacuum, recrystallizing coarse product in ethanol, and drying to obtain 2,6-bis(2-benzimidazolyl)pyridine which is white solid. The 2,6-bis(2-benzimidazolyl)pyridine yield is 85.2 to 91.4 percent, and the purity of the 2,6-bis(2-benzimidazolyl)pyridine is over 98 percent. The method has the advantages of simple and convenient operation, easy product separation and purification, high yield and low cost.

Description

technical field [0001] The invention relates to an aromatic organic compound, in particular to a preparation method of 2,6-dibenzimidazolylpyridine. Background technique [0002] As an important fine chemical intermediate, 2,6-dibenzimidazolylpyridine is widely used in the synthesis and preparation of medicines, pesticides, dyes, luminescent materials, solar cells, etc. At present, the preparation methods of 2,6-dibenzimidazolylpyridine reported at home and abroad mainly include the following aspects: (1) take benzimidazole and 2,6-dichloropyridine as raw materials, and prepare 2 , 6-dibenzimidazolylpyridine (Organometallics, 2009, 28(6), 1965-1968). The preparation method is complicated to operate, and the sodium hydride used in the preparation process belongs to wet and flammable materials, and the reaction conditions are harsh; at the same time, the temperature needs to be continuously changed during the preparation process, which is difficult to control and is not condu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14
Inventor 张昭苏瑞飞
Owner SHANXI UNIV