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Hexa-aromatic heterocyclic diamine and preparation method thereof

A technology for aromatic heterocycle and diazepine, which is applied in the field of six-membered aromatic heterocyclic diamine and its preparation, and can solve the problems of low yield and the like

Inactive Publication Date: 2010-06-16
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, the ring-forming reaction of synthetic phenylpyridine structure can also adopt the ring-closure reaction (Marcoux, J.F.; Marcotte, F.A.; J.Org.Chem., 2001 , 66, 4194-4199), but the yield is only 15%
[0007] So far, no literature has reported the synthesis of nonlinear isomeric diamines containing 2,5-disubstituted pyridine or 2,5-disubstituted pyrimidine structures

Method used

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  • Hexa-aromatic heterocyclic diamine and preparation method thereof
  • Hexa-aromatic heterocyclic diamine and preparation method thereof
  • Hexa-aromatic heterocyclic diamine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Example 1: Add m-nitroacetophenone (16.5g, 0.1mol), N,N,N',N'-tetramethyl-3-nitro-1,5-diazapentane to the reaction vessel Diene tetrafluoroborate (25.9 g, 0.1 mol) and 64.8 g dimethylformamide. Under mechanical stirring, potassium tert-butoxide (22.4 g, 0.2 mol) was added and stirred at 40° C. for 2 hours. Then, ammonium acetate (46.2 g, 0.6 mol) and glacial acetic acid (36.0 g, 0.6 mol) were added, and the temperature was raised to 100° C. to react for 6 hours. Cool to room temperature and filter off the solid. The solid was washed with water and ethanol and dried to obtain 2-(3-nitrophenyl)-5-nitropyridine;

[0064] The 2-(3-nitrophenyl)-5-nitropyridine obtained above was added to 16.5 g of ethanol, 0.165 g of palladium on carbon and hydrazine hydrate (5.0 g, 0.1 mol) were added, and heated to reflux for 6 hours. The palladium carbon was filtered out while it was hot, and after the filtrate was cooled to room temperature, the product was precipitated. After filtra...

Embodiment 2

[0065] Example 2: Add m-nitroacetophenone (16.5g, 0.1mol), N,N,N',N'-tetrabutyl-3-(3-nitrophenyl)-1 to the reaction vessel, 5-diazapentadiene perchloric acid (51.6 g, 0.1 mol) and 421 g dimethylacetamide solvent. Under mechanical stirring, sodium methoxide (16.2 g, 0.3 mol) was added and stirred at 10° C. for 4 hours. Then, ammonium acetate (7.7 g, 0.1 mol) and glacial acetic acid (60.0 g, 1.0 mol) were added, and the temperature was raised to 110° C. for 1 hour. Cool to room temperature and filter off the solid. The solid was washed with water and ethanol and dried to obtain 2,5-bis[(3-nitrophenyl)]pyridine, which was directly used in the next step;

[0066] Add the 2,5-bis[(3-nitrophenyl)]pyridine obtained above into 165 g of ethanol, add 1.65 g of palladium on carbon, and hydrazine hydrate (50.0 g, 1.0 mol), and heat to reflux for 10 hours. The palladium carbon was filtered out while it was hot, and after the filtrate was cooled to room temperature, the product was preci...

Embodiment 3

[0067] Example 3: Add m-nitroacetophenone (16.5g, 0.1mol), N,N,N',N'-tetraoctyl-3-(4-nitrophenyl)-1 to the reaction vessel, 5-diazapentadiene perchlorate (74.0 g, 0.1 mol) and 1353 g isopropanol. Under mechanical stirring, potassium tert-butoxide (44.8 g, 0.4 mol) was added, and stirred at 60° C. for 1 hour. Then, ammonium acetate (77.0 g, 1.0 mol) and glacial acetic acid (6.0 g, 0.1 mol) were added, and the temperature was raised to 80° C. for 10 hours. Cool to room temperature and filter off the solid. The solid was washed with water and ethanol and dried to obtain 2-(3-nitrophenyl)-5-(4-nitrophenyl)pyridine, which was directly used in the next step;

[0068] Add 2-(3-nitrophenyl)-5-(4-nitrophenyl)pyridine obtained above into 80 g of ethanol, add 0.825 g of palladium carbon, hydrazine hydrate (15.0 g, 0.3 mol), and heat to reflux for 5 Hour. The palladium carbon was filtered out while it was hot, and after the filtrate was cooled to room temperature, the product was prec...

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Abstract

The invention provides aromatic heterocyclic diamine which contains pyridine or pyrimidine. A synthesis method of the provided aromatic heterocyclic diamine comprises: synthesizing nonlinear isomer of the aromatic heterocyclic diamine by using raw materials which are low in price and easily obtained instead of precious metal catalyst and other expensive raw materials; and the yield reaches up to 70-85%. The aromatic heterocyclic diamine can be applied to synthesize heat-resistant high polymer material isomeric polyimide, thus improving the processing performance of the polyimide.

Description

technical field [0001] The invention relates to a six-membered aromatic heterocyclic diamine and a preparation method thereof. Background technique [0002] Polyimide is a kind of heat-resistant polymer material with excellent comprehensive performance. It not only has high thermal performance, mechanical performance and chemical stability, but also has low dielectric constant and thermal expansion coefficient, making it widely used in aviation and aerospace. Industry, microelectronics industry and many other fields have been widely used. Numerous studies have shown that the unique properties of polyimide are determined by its polymer chain structure, and the structural characteristics of diamine monomers have a great impact on the performance of the final polyimide. [0003] Introducing some nitrogen-containing aromatic heterocyclic structures in the form of diamine monomers in the main chain of polyimide is a new method to improve the heat resistance and mechanical proper...

Claims

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Application Information

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IPC IPC(8): C07D213/73C07D213/38C07D239/42C07D239/26
Inventor 郭海泉邱雪鹏康传清金日哲姚海波高连勋
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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