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Non-coplanar benzimidazole diamine and preparation method thereof

A benzimidazole diamine, non-coplanar technology, which is applied in the field of non-coplanar benzimidazole diamine and its preparation, can solve the problems of few types of non-coplanar benzimidazole diamine, unsatisfactory, single structure and the like, Achieve the effect of improving optical properties and solubility, reducing conjugation effect and overcoming single structure

Inactive Publication Date: 2021-04-06
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As mentioned in the document "Synthesis and Characterization of ThermallyStable, High-Modulus Polyimides Containing Benzmidazole Moieties, SHUANG WANG, etc., "Journal of Polymer Science: Part A: Polymer Chemistry" No. 47, pp. 2024-2031, 2009" The synthesis of imidazole monomers, and mentioned that the materials prepared by using benzimidazole monomers have excellent thermal and mechanical properties, but the optical properties of the materials are extremely poor due to the conjugation effect of benzimidazole diamine monomers. Difference
However, at present, the benzimidazole diamine monomer structure in this field is relatively single, and there are fewer types of non-coplanar benzimidazole diamines, resulting in single performance of the prepared polymer material, which cannot meet the requirements of synthesizing polymers with different properties. Moreover, the optical properties of polymers are generally not high, and the construction of non-coplanar diamine monomers with different structures is a research hotspot in this field.

Method used

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  • Non-coplanar benzimidazole diamine and preparation method thereof
  • Non-coplanar benzimidazole diamine and preparation method thereof
  • Non-coplanar benzimidazole diamine and preparation method thereof

Examples

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preparation example Construction

[0046] The present invention provides the preparation method of non-coplanar benzimidazole diamine described in the above scheme, comprising the following steps:

[0047] (1) performing a condensation reaction between a compound having a structure shown in formula a and a compound having a structure shown in formula b, and subjecting the resulting condensation product to a ring-closing reaction to obtain a compound having a structure shown in formula c;

[0048]

[0049] The types of X and Y in formula a to formula c are consistent with those in formula I;

[0050] (2) Under the condition of hydrogen, the compound having the structure shown in formula c is subjected to catalytic hydrogenation reaction to obtain the non-coplanar benzimidazole diamine having the structure shown in formula I.

[0051] The synthetic route of the present invention's synthetic non-coplanar benzimidazole diamine is shown in formula A, and is specifically described below in conjunction with formula...

Embodiment 1

[0069] In this example, the specific structure of the non-coplanar benzimidazole diamine is as follows, and the Chinese name is 5-amino-2-(2-methyl-4-aminobenzene)-1-phenylbenzimidazole:

[0070]

[0071] The preparation method of above-mentioned 5-amino-2-(2-methyl-4-aminobenzene)-1-phenylbenzimidazole is as follows:

[0072] (1) Add 50.0g of N-phenyl-4-nitrobenzene-1,2-diamine, 33.1g of triethylamine and 500.0g of dichloromethane into the reaction flask, cool down to 5±1°C, and drop 52.1 g 3-methyl-4-nitrobenzoyl chloride, the dropwise addition was completed in 2-3 hours, reacted at room temperature for 16 hours, and TLC confirmed that the reaction was complete. Add 1000.0g of water to the reaction system, filter under reduced pressure to obtain 85.6g of crude product, add 800.0g of butyrolactone and 45.0g of p-toluenesulfonic acid after drying, react at 200°C for 4h, TLC confirms that the reaction is complete, cool down to 0~ 5°C, add 1400.0g water to the reaction syste...

Embodiment 2

[0075] In this example, the specific structure of the non-coplanar benzimidazole diamine is as follows, and the Chinese name is 5-amino-2-(2-trifluoromethyl-4-aminobenzene)-1-phenylbenzimidazole:

[0076]

[0077] The preparation method of above-mentioned 5-amino-2-(2-trifluoromethyl-4-aminobenzene)-1-phenylbenzimidazole is as follows:

[0078] (1) Add 50.0g N-phenyl-4-nitrobenzene-1,2-diamine, 25.9g pyridine and 500.0g dichloromethane to the reaction flask, cool down to 5±1°C, add dropwise 66.3g 3- Trifluoromethyl-4-nitrobenzoyl chloride was added dropwise in 2-3 hours, and reacted at room temperature for 16 hours, and TLC confirmed that the reaction was complete. Add 1000.0g water to the reaction system, filter under reduced pressure to obtain 97.0g crude product, add 1000.0g sulfolane and 21.8mL concentrated hydrochloric acid after drying, react at 200°C for 4h, TLC confirms that the reaction is complete, cool down to 0-5°C, and pour Add 1400.0 g of water to the reactio...

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Abstract

The invention relates to the technical field of organic synthesis, and provides non-coplanar benzimidazole diamine and a preparation method thereof. The novel benzimidazole diamine has side groups on a benzimidazole ring and a benzene ring, the introduction of double side groups promotes the torsion of the benzimidazole ring and the benzene ring to form a non-coplanar surface, so the conjugation effect in molecules is reduced, and the optical performance and solubility of a polymeric material prepared from a diamine monomer are further improved; and besides, the types of side groups introduced to the benzimidazole ring and the benzene ring are variable, so various polymeric materials with different structures and properties can be obtained and have wide application prospects. According to the preparation method provided by the invention, the non-coplanar benzimidazole diamine can be obtained through a a condensation reaction, a ring closing reaction and a catalytic hydrogenation reaction; raw materials are cheap and easy to obtain; process safety is high; operation is simple and convenient; production cost is relatively low; reaction yield is relatively high; and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a non-coplanar benzimidazole diamine and a preparation method thereof. Background technique [0002] Diamine compounds are an important class of chemical raw materials or intermediates, which can 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] The introduction of benzimidazole diamine as a typical rigid aromatic heterocyclic unit into the polymer backbone can significantly improve the mechanical properties and heat resistance of materials. As mentioned in the document "Synthesis and Characterization of ThermallyStable, High-Modulus Pol...

Claims

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Application Information

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IPC IPC(8): C07D235/18
CPCC07D235/18
Inventor 陈春海钱广涛于有海陈海权代凤娜闫晓莹
Owner DONGHUA UNIV
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