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2,4-di (4-carboxyphenyl)-6-phenyl-1,3,5-triazine, derivative and preparation method thereof

A technology of methyl carboxyl and derivatives, applied in the field of organic synthesis, to achieve the effects of convenient operation, high yield and short cycle

Inactive Publication Date: 2012-06-13
CENT SOUTH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] So far, the method for preparing 2,4-bis(4-methylcarboxyphenyl)-6-phenyl-1,3,5-triazine and its derivatives has not been reported in any published publications

Method used

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  • 2,4-di (4-carboxyphenyl)-6-phenyl-1,3,5-triazine, derivative and preparation method thereof
  • 2,4-di (4-carboxyphenyl)-6-phenyl-1,3,5-triazine, derivative and preparation method thereof
  • 2,4-di (4-carboxyphenyl)-6-phenyl-1,3,5-triazine, derivative and preparation method thereof

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preparation example Construction

[0032] 2,4-bis(4-methylcarboxyphenyl)-6-phenyl-1,3,5-triazine and its derivatives as shown in general formula I provided by the present invention, its synthetic method specifically comprises the following stages :

[0033] (1) The preparation of Grignard reagent: under inert gas protection, as shown in general formula III and IV 4-alkylphenyl halides and phenyl halides or derivatives thereof, respectively with sufficient metal magnesium at 0 The reaction at -80°C takes 4-20 hours, and ethers are used as solvents to obtain a dark brown solution, and the corresponding Grignard reagents 4-alkylphenylmagnesium halide and phenylmagnesium halide are obtained. Wherein, the inert gas used is nitrogen, argon, etc.;

[0034] (2) Preparation of 2,4 bis(4-alkylphenyl)-6-chloro-1,3,5-triazine: ether of 2,4,6-trichloro-1,3,5-triazine The solution was added dropwise in batches to the ether solution of the above-mentioned 4-alkylphenylmagnesium halide, and the molar ratio of reactants was d...

example 1

[0044] Example 1: Preparation of 2,4-bis(4-methylcarboxyphenyl)-6-phenyl-1,3,5-triazine

[0045] In a 500mL three-necked flask equipped with electromagnetic stirring, a thermometer, a reflux condenser and a drying tube, 5.1g (27.1mmol) of cyanuric chloride and 15mL of tetrahydrofuran (THF) were sequentially added. Under the protection of an ice bath, 10.6 g (54.2 mmol) of Grignard reagent 4-methylphenylmagnesium bromide prepared in advance and cooled was added dropwise in batches. After the addition was completed, the reaction was stirred for 20 minutes, and the temperature was raised to 25°C for 12 hours. Then the temperature was raised to 50°C and the reaction lasted 12h. Cool and protect it with an ice bath, then add dropwise 4.9 g (27.2 mmol) of Grignard reagent phenylmagnesium bromide prepared in advance and cooled. The reaction was stirred for 30 min, and then the system was heated to 85° C. for 12 h to obtain a tan oily liquid. The reaction product was subjected to r...

experiment example 1

[0060] Experimental Example 1: Preparation of polyarylamide containing 1,3,5-triazine

[0061] In a three-neck flask equipped with a mechanical stirrer, a condenser and a nitrogen conduit, 20.0 mmol (7.938 g) of 2,4-bis(4-methylcarboxyphenyl)-6-phenyl-1,3 , 5-triazine, 18.0mmol (3.604g) 4,4-diaminodiphenyl ether, 86.0mmol (9.546g) anhydrous calcium chloride, 40.0mmol (12.411g) triphenyl phosphite, 20mL pyridine and 60mL N-methylpyrrolidone (NMP). After reacting at 110° C. for about 6 h, it was cooled to room temperature. The reaction solution was poured into ethanol and water mixed solution (1:1, V / V) for sedimentation, and the deionized water was continuously stirred during the pouring process, and finally a white fibrous polymer was obtained. The product is filtered, washed with water and washed with alcohol. The polymer was dissolved in NMP as solvent and vacuum filtered. The filtrate was settled into a mixture of ethanol and water (1:1, V / V), filtered under vacuum, and...

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Abstract

The invention relates to a 2,4-di (4-carboxyphenyl)-6-phenyl-1,3,5-triazine, a derivative and a preparation method thereof. The preparation method comprises the following steps of: reacting 2,4,6-trichloro-1,3,5-triazine under the actions of 4-alkyl phenyl magnesium halide as a Grignard reagent, phenyl magnesium halide or a derivative thereof; and oxidizing with a catalyst to prepare a compound disclosed by a formula I. The compound of the formula I can be used as a useful organic or medicine intermediate and is an important monomer for preparing 1, 3, 5-triazine high-performance polymer, wherein R stands for hydrogen, phenyl, naphthyl or a linear chain with 1-10 carbon atoms or alkoxyl with a branched chain.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to 2,4-bis(4-methylcarboxyphenyl)-6-phenyl-1,3,5-triazine and its derivatives and their preparation methods. Background technique [0002] Aryl-1,3,5-triazine and its derivatives are important organic and pharmaceutical intermediates. Among them, the aryl-1,3,5-triazine containing two functional groups can also be used as an antitumor drug or an ultraviolet stabilizer. In addition, with the rapid development of aerospace, military, machinery, electronic appliances and other fields, the demand for high-performance polymer materials is becoming increasingly urgent. Polymers containing 1,3,5-triazine structure can be used as high-performance engineering plastics and electron transport materials due to their excellent comprehensive properties such as high temperature resistance, high strength, good flame retardancy, and unique optical and electrochemical properties. And sep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D251/24
CPCY02P20/582
Inventor 喻桂朋潘春跃李彬赵菲
Owner CENT SOUTH UNIV
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