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N-substituted benzimidazole diamine and preparation method thereof

A technology of benzimidazole diamine and dinitro, which is applied in the field of diamine compounds and their preparation, can solve the problems of harsh conditions and high reaction temperature, and achieves the effects of easy industrialization, high reaction yield and low energy consumption

Inactive Publication Date: 2019-03-01
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to provide a kind of N-substituted benzimidazole diamine and its preparation and application, to overcome the defects of high preparation reaction temperature and harsh conditions in the prior art, and the present invention provides a kind of N-substituted benzimidazole diamine with lower energy consumption, A more industrialized synthesis method, using milder acetic acid as a catalyst, and performing ring-closing reaction at a lower temperature of 80-120°C

Method used

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  • N-substituted benzimidazole diamine and preparation method thereof
  • N-substituted benzimidazole diamine and preparation method thereof
  • N-substituted benzimidazole diamine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] In this example, the specific structure of N-substituted benzimidazole diamine is as follows:

[0047]

[0048] The preparation method of above-mentioned 5-amino-2-(4-aminobenzene)-1-methylbenzimidazole is as follows:

[0049] a. Add 50.0g N-methyl-4-nitrobenzene-1,2-diamine, 33.3g triethylamine and 500.0g tetrahydrofuran to the reaction flask, cool down to 5±1°C, add 61.0g p-nitro Benzoyl chloride was added dropwise in 2-3 hours, reacted at room temperature for 16 hours, and TLC confirmed that the reaction was complete. Add 1500.0g of water to the reaction system, filter under reduced pressure to obtain 90.0g of crude product, add 900.0g of acetic acid after drying, react at 100°C for 16h, TLC confirms that the reaction is complete, cool down to 0-5°C, and add 1400.0g water, dried under reduced pressure suction filtration, recrystallized from dimethylformamide, filtered, dried to obtain 74.3g 5-nitro-2-(4-nitrobenzene)-1-methylbenzimidazole, yield : 83.3%, confirm...

Embodiment 2

[0052] In this example, the specific structure of N-substituted benzimidazole diamine is as follows:

[0053]

[0054] The preparation method of above-mentioned 5-amino-2-(4-aminobenzene)-1-phenylbenzimidazole is as follows:

[0055]a. Add 50.0g N-phenyl-4-nitrobenzene-1,2-diamine, 19.0g pyridine and 500.0g dichloromethane to the reaction flask, cool down to 5±1℃, add 44.5g p-nitro Benzoyl chloride was added dropwise in 2-3 hours, reacted at room temperature for 16 hours, and TLC confirmed that the reaction was complete. Add 1500.0g of water to the reaction system, filter under reduced pressure to obtain 78.0g of crude product, add 700.0g of acetic acid after drying, react at 80°C for 16h, TLC confirms that the reaction is complete, cool down to 0-5°C, and add 1400.0g water, dried under reduced pressure suction filtration, recrystallized from dimethylformamide and water, filtered, dried to obtain 67.0g 5-nitro-2-(4-nitrobenzene)-1-phenylbenzimidazole, The yield was 85.3%,...

Embodiment 3

[0058] In this example, the specific structure of N-substituted benzimidazole diamine is as follows:

[0059]

[0060] The preparation method of above-mentioned 5-amino-2-(4-aminobenzene)-1-(2-fluorophenyl)-phenylbenzimidazole is as follows:

[0061] a. Add 50.0g N-(2-fluorophenyl)-4-nitrobenzene-1,2-diamine, 22.5g triethylamine and 500.0g toluene to the reaction flask, cool down to 5±1℃, add dropwise 41.4g of p-nitrobenzoyl chloride was added dropwise within 2 to 3 hours, reacted at room temperature for 16 hours, and TLC confirmed that the reaction was complete. Add 1500.0g of water to the reaction system, filter under reduced pressure to obtain 75.0g of crude product, add 700.0g of sulfuric acid after drying, react at 120°C for 16h, TLC confirms that the reaction is complete, cool down to 0-5°C, and pour into the reaction system 2000.0g of water, dried under reduced pressure suction filtration, recrystallized from dimethylacetamide, filtered, and dried to obtain 65.0g of...

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Abstract

The invention relates to N-substituted benzimidazole diamine and a preparation method thereof. The structure is shown as a general formula I. The preparation method includes conducting condensation and ring closing reaction through general formulas II and III and then conducting reduction reaction to obtain the N substituted benzimidazole diamine. A plurality of functional groups can be introducedat the N atom of benzimidazole, which brings different structures and properties to the material. The N-substituted benzimidazole diamine has short synthetic route, low cost and easy availability ofraw materials, high process safety, simple operation, low production cost and high reaction yield, thereby being suitable for industrial production.

Description

technical field [0001] The invention belongs to diamine compounds and a preparation method thereof, in particular to an N-substituted benzimidazole diamine and a preparation method thereof. Background technique [0002] Diamine compounds are a class of important chemical raw materials or intermediates, and they can also be used as monomers to synthesize new polyimides, polyamides, polyureas, silicones and other polymers. The introduction of the aromatic heterocyclic structure in the diamine can effectively improve the mechanical properties, chemical corrosion resistance, high temperature resistance, and flame resistance of the material, thereby expanding the application field of the material. [0003] Among them, benzimidazole diamine, as a typical rigid aromatic heterocyclic unit, is introduced into the main chain of the polymer, which can significantly improve the mechanical properties and heat resistance of the material. [0004] Wang Shuang et al. (Journal of Polymer Sc...

Claims

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Application Information

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IPC IPC(8): C07D235/18
CPCC07D235/18
Inventor 李慧钱广涛陈春海陈海权姚佳楠顾洋洋
Owner DONGHUA UNIV
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