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Method for preparing 3-substituted-2,5-diphenyltetrazolium chloride catalyzed by copper Lewis acid surfactant

A technology of diphenyltetrazolium and surfactant, applied in the field of organic synthesis, can solve the problems of high equipment quality requirements, complicated post-processing operations, inability to industrialize, etc., and achieves reduced production equipment requirements, simple and easy operation, safety, The effect of simplified reaction steps

Active Publication Date: 2021-02-23
湖北佰智昂生物化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The invention provides a method for preparing chlorinated-3-substituted-2,5-diphenyltetrazolium compounds catalyzed by a copper Lewis acid surfactant, aiming to overcome the following deficiencies in the prior art at least to a certain extent : The preparation process contains multiple steps, the post-processing operation is complicated, and a large amount of chemical waste is generated, which leads to high production costs and cannot be industrialized; hydrogen chloride or chlorine gas is used as the chlorination reagent, which requires high equipment quality and there is a potential risk of leakage

Method used

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  • Method for preparing 3-substituted-2,5-diphenyltetrazolium chloride catalyzed by copper Lewis acid surfactant
  • Method for preparing 3-substituted-2,5-diphenyltetrazolium chloride catalyzed by copper Lewis acid surfactant
  • Method for preparing 3-substituted-2,5-diphenyltetrazolium chloride catalyzed by copper Lewis acid surfactant

Examples

Experimental program
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Effect test

Embodiment 1

[0058]

[0059] A preparation method of chlorinated-3-substituted-2,5-diphenyltetrazolium compound V-1, the steps of which are:

[0060] A. Add benzaldehyde I (0.1mol, 10.6g), phenylhydrazine II (0.1mol, 10.8g), aniline III-1 (0.1mol, 9.3g), sodium nitrite (0.12mol, 8.3g) into the reaction vessel ) and 100mL water, stirred and mixed at room temperature;

[0061] B. Add copper Lewis acid surfactant Cu(OSO 2 C 12 h 25 ) 2 , (0.01mol, 5.6g);

[0062] C. Fully stir the reaction at room temperature, and the reaction time is 2h;

[0063] D. Cool the mixed solution obtained in step C to below 5°C, cool and recrystallize, and obtain solid 2,3,5-triphenylformazan IV-130.0g after filtration, wash the solid with water and recover the filtrate, the filtrate Centrifuge at 1000-1600rpm to separate the white turbid liquid (lower layer) and cool it down to below 10°C. It can be recrystallized to obtain a white solid, which is the recovered copper Lewis acid surfactant Cu(OSO 2 C 12...

Embodiment 2

[0070]

[0071] A preparation method of chloro-3-p-methylphenyl-2,5-diphenyltetrazolium compound V-2, the steps are:

[0072] A. Add benzaldehyde I (0.1mol, 10.6g), phenylhydrazine II (0.1mol, 10.8g), p-methylaniline III-2 (0.1mol, 10.7g), sodium nitrite (0.12mol , 8.3g) and 100mL water, stirred and mixed at room temperature;

[0073] B. Add copper Lewis acid surfactant Cu(OSO 2 C 12 h 25 ) 2 , (0.01mol, 5.6g);

[0074] C. Fully stir the reaction at room temperature, and the reaction time is 2h;

[0075] D. Cool the mixed solution obtained in step C to below 5°C, cool and recrystallize, and obtain solid 3-p-methylphenyl-2,5-diphenylformazan IV-231.0g after filtration, wash the solid with water And recover the filtrate, the filtrate is centrifuged at 1000-1600rpm, the white turbid liquid (lower layer) is separated and cooled to below 10°C, and can be recrystallized to obtain a white solid, which is the recovered copper Lewis acid surfactant Cu(OSO 2 C 12 h 25 ) 2 ,...

Embodiment 3

[0082]

[0083] A preparation method of chloro-3-p-methoxyphenyl-2,5-diphenyltetrazolium compound V-3, the steps are:

[0084] A. Add benzaldehyde I (0.1mol, 10.6g), phenylhydrazine II (0.1mol, 10.8g), p-methoxyaniline III-3 (0.1mol, 12.3g), sodium nitrite (0.12 mol, 8.3g) and 100mL water, stirred and mixed at room temperature;

[0085]B. Add copper Lewis acid surfactant Cu(OSO 2 C 12 h 25 ) 2 , (0.01mol, 5.6g);

[0086] C. Fully stir the reaction at room temperature, and the reaction time is 1h;

[0087] D. Cool the mixed solution obtained in step C to below 5°C, cool and recrystallize, and filter to obtain 333.0 g of solid 3-p-methoxyphenyl-2,5-diphenylformazan IV-3, which is washed with water Solid and recover the filtrate, the filtrate is centrifuged at 1000-1600rpm, the white turbid liquid (lower layer) is separated and cooled to below 10°C, and the white solid can be recrystallized, which is the recovered copper Lewis acid surfactant Cu(OSO 2 C 12 h 25 ) 2 ,...

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Abstract

The invention belongs to the technical field of organic synthesis, and specifically relates to a method for preparing chlorinated-3-substituted-2,5-diphenyltetrazolium compounds using a copper Lewis acid surfactant as a catalyst, comprising the following steps: 1 ) with copper Lewis acid surfactant Cu(OSO 2 C n h 2n+1 ) 2 As a catalyst, benzaldehyde, phenylhydrazine, arylamine and sodium nitrite react in solvent water to obtain 3-aryl-2,5-diphenylformazan; 2) 3-aryl-2,5-diphenyl Formazan is in the mixed solvent of dichloromethane and water, under the condition of solid chlorination reagent N-chlorosuccinimide, carry out ring closure and chlorination, obtain chlorinated-3-aryl-2,5- Diphenyltetrazolium. The method uses a "one-pot method" continuous strategy to complete the three-step transformation, which not only omits the intermediate separation step, but also has simple purification steps and is easy to operate.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing chlorinated-3-substituted-2,5-diphenyltetrazolium compounds by using a copper Lewis acid surfactant as a catalyst. Background technique [0002] Chlorinated-3-substituted-2,5-diphenyltetrazolium compounds are widely used in the fields of biochemistry, pharmaceutical science, medicine, agriculture, high-energy materials, automobile industry and photography. Among them, 2,3,5-triphenyltetrazolium chloride (TTC for short) is often used as an analytical reagent and a chromatographic reagent, for example, it can be used to detect the vitality of seeds and the ischemic infarction of mammalian tissues. In addition, TTC can also be used as a corrosion inhibitor that mainly inhibits the anodic process, and is used to prevent the contact between the corrosive acidic solution and the steel surface and play a role in corrosion inhibition. Therefo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D257/04
CPCC07D257/04
Inventor 李清平徐志丹
Owner 湖北佰智昂生物化工有限公司