Method for preparing 5-substituted tetrazole compound and product obtained by method

A compound, tetrazolium technology, applied in the field of preparation of 5-substituted tetrazolium compounds, can solve the problems of complex post-processing operations, long reaction time, low reactivity, etc., achieve simplified separation and purification steps, and reduce reaction time , The effect of reducing the amount of catalyst

Pending Publication Date: 2022-05-13
HUBEI ENG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] This method has low reactivity, requires a long reaction time (24h) and a high temperature (100°C), and the post-treatment operations of the reaction are very complicated, and an equivalent amount of zinc reagent must be used, resulting in a large amount of waste. This limits the application of such methods in actual production
[0010] The invention provides a novel method for preparing 5-substituted tetrazole compounds, which solves the problems in the existing production process well

Method used

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  • Method for preparing 5-substituted tetrazole compound and product obtained by method
  • Method for preparing 5-substituted tetrazole compound and product obtained by method
  • Method for preparing 5-substituted tetrazole compound and product obtained by method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047]

[0048] A kind of preparation method of 5-substituted tetrazole compound II-1, its steps are:

[0049] A. Add ethyl thiocyanate (0.1mol, 8.7g), sodium azide (0.12mol, 7.8g) and water (300ml) in the reaction vessel, fully stir at room temperature to obtain a mixed solution;

[0050] B. add chitosan immobilized zinc catalyst (10.0mg) in the mixed solution in A;

[0051] C. stirring reaction at room temperature, the reaction time is 1h;

[0052] D. Add hydrobromic acid dropwise to the mixed solution obtained in step C, adjust the pH to about 1;

[0053] E. filtering and separating the solid catalyst;

[0054] F. Cool the clear solution (upper layer) separated in step E to below 5°C, and recrystallize to obtain 12.0 g of 5-ethylthiotetrazolium compound II-1, with a yield of 92%;

[0055] G. The chitosan immobilized zinc catalyst that reclaims, recyclable, reclaims 9.9mg altogether, reclaims the productive rate that carries out reaction for seven times and is respecti...

Embodiment 2

[0060]

[0061]A kind of preparation method of 5-substituted tetrazole compound II-2, its steps are:

[0062] A. Add methyl thiocyanate (0.1mol, 7.3g), sodium azide (0.12mol, 7.8g) and water (300ml) in the reaction vessel, fully stir at room temperature to obtain a mixed solution;

[0063] B. add chitosan immobilized zinc catalyst (10mg) in the mixed solution in A;

[0064] C. stirring reaction at room temperature, the reaction time is 0.5h;

[0065] D. Add hydrobromic acid dropwise to the mixed solution obtained in step C, adjust the pH to about 1;

[0066] E. filtering and separating the solid catalyst;

[0067] F. Cool the clear solution (upper layer) separated in step E to below 5°C, and recrystallize to obtain 10.2 g of 5-methylthiotetrazolium compound II-2, with a yield of 93%;

[0068] G. The chitosan immobilized zinc catalyst that reclaims, recyclable, reclaims 9.2mg altogether, reclaims the productive rate that carries out reaction for seven times and is respect...

Embodiment 3

[0073]

[0074] A preparation method of 5-substituted tetrazole compound II-3, the steps are:

[0075] A. Add phenyl thiocyanate (0.1mol, 13.5g), sodium azide (0.12mol, 7.8g) and water (300ml) in the reaction vessel, fully stir at room temperature to obtain a mixed solution;

[0076] B. add chitosan immobilized zinc catalyst (10mg) in the mixed solution in A;

[0077] C. stirring reaction at room temperature, the reaction time is 0.5h;

[0078] D. Add hydrobromic acid dropwise to the mixed solution obtained in step C, adjust the pH to about 1;

[0079] E. filtering and separating the solid catalyst;

[0080] F. Cool the clear solution (upper layer) separated in step E to below 5°C, and recrystallize to obtain 16.9 g of 5-phenylthiotetrazolium compound II-3, with a yield of 95%;

[0081] G. The chitosan immobilized zinc catalyst that reclaims, recyclable, reclaims 9.2mg altogether, reclaims the productive rate that carries out reaction for seven times and is respectively:...

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PUM

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a method for preparing a 5-substituted tetrazole compound and a product obtained by the method. According to the invention, the 5-substituted tetrazole compound can be prepared by using the chitosan immobilized zinc catalyst as a heterogeneous catalyst at room temperature in a water phase and an air atmosphere. The technical scheme has a series of advantages of mild conditions, environment friendliness, high reaction activity, convenience in product separation, capability of recycling the catalyst and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing a 5-substituted tetrazole compound and a product obtained therefrom. Background technique [0002] 5-Substituted tetrazole compounds are intermediates widely used in pharmaceutical production. For example, this type of compound can be applied to the production of losartan and candesartan drugs for the treatment of hypertension, diabetes and congestive heart failure. The 5-substituted tetrazole compound can also be used in the synthesis of a new generation of cephalosporin antibiotics and as an intermediate in the synthesis of antifungal drugs. In addition, the 5-substituted tetrazole compound can be used as a photosensitizer to improve the stability of the silver halide photosensitizer during storage. [0003] The existing method for preparing 5-substituted tetrazole compounds mainly uses divalent zinc as a catalyst for heterogeneous catalysis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/04
CPCC07D257/04
Inventor 朱磊李博解张瑶瑶李清平徐志丹陈舒晗张泽浪赵雪
Owner HUBEI ENG UNIV
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