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Chemical synthesizing method of tetrazole compound

A technology of chemical synthesis and tetrazolium, applied in the direction of organic chemistry, can solve problems such as environmental pollution, troublesome operation, hidden safety hazards, etc., and achieve the effect of high reaction yield, low production cost, and no three wastes

Inactive Publication Date: 2006-05-24
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this reaction route still has major disadvantages: firstly, the amine needs to be made into hydrochloride for reaction, and the operation is relatively troublesome; secondly, there are strong acidic media such as hydrochloric acid and acetic acid in the reaction system and the action of sodium azide will still cause severe Toxic and explosive azide gas is released, which makes the reaction have a greater safety hazard; thirdly, excessive acetic acid is difficult to recover and purify by distillation, which is easy to cause environmental pollution
Therefore, many problems that exist in this reaction route remain to be improved

Method used

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  • Chemical synthesizing method of tetrazole compound
  • Chemical synthesizing method of tetrazole compound
  • Chemical synthesizing method of tetrazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The feed ratio is amine: orthocarboxylate: metal azide: ytterbium trifluoromethanesulfonate=1: 1: 1: 0.02 (mol ratio), amine is aniline, and orthocarboxylate is triethyl orthoformate, The azide metal salt is sodium azide, and chloroform is used as an organic solvent, and its consumption is 10 times that of aniline.

[0033] In a 150ml four-neck flask equipped with a thermometer, a reflux condenser and mechanical stirring, add aniline 4.56ml (50mmol) at room temperature, sodium azide 3.25g (50mmol), triethyl orthoformate 8.34ml (50mmol), Ytterbium trifluoromethanesulfonate 0.62g (1mmol), dissolve with chloroform 46g, add, be warming up to 60 ℃, and react 3 hours at 60~65 ℃, follow and monitor with HPLC simultaneously (flow velocity: 1.5ml / min, acetonitrile: Water: acetic acid = 20:80:0.05), after the reaction was completed, the solvent was evaporated, and under ice cooling, 20ml of ice water was slowly added, stirred continuously for 10min, and extracted three times with...

Embodiment 2

[0037] The feed ratio is amine: orthocarboxylate: metal azide: ytterbium trifluoromethanesulfonate=1: 1: 1: 0.02 (mol ratio), amine is aniline, and orthocarboxylate is triethyl orthoformate, The azide metal salt is sodium azide, and chloroform is used as an organic solvent, and its consumption is 8 times that of aniline.

[0038] Other operations are the same as in Example 1, the product yield is 81.1%, the purity is 99.6%, the melting point is 64.7-65.1°C, and the recovery rate of ytterbium trifluoromethanesulfonate is 94.2%.

Embodiment 3

[0040] The feed ratio is amine: orthocarboxylate: metal azide: ytterbium trifluoromethanesulfonate=1: 1: 1: 0.02 (mol ratio), amine is aniline, and orthocarboxylate is triethyl orthoformate, The azide metal salt is sodium azide, and chloroform is used as an organic solvent, and its consumption is 5 times that of aniline.

[0041] Other operations are the same as in Example 1, the product yield is 80.5%, the purity is 99.7%, the melting point is 64.5-65.0°C, and the recovery rate of ytterbium trifluoromethanesulfonate is 95.1%.

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Abstract

The invention relates to a chemical method for synthesizing tetrazole compound, including the steps as follows: making amine and crude carboxylic ester reacts with nitrine metallic salt in organic solvent at 20 deg.C-150 deg.C under the action of a catalyst ytterbium trifluoro methyl sulfonate, and afterprocessing to obtain the target product. The synthesizing method has the advantages of reasonable technique, high reaction yield, less catalyst dosage, low production cost, no three wastes, and being able to conveniently recover and use indiscriminately.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of tetrazole compounds. (2) Background technology [0002] Before the present invention was made, the chemical synthesis methods of tetrazole compounds in the prior art were mainly prepared by using traditional Bronsted acids such as acetic acid and trifluoroacetic acid as catalysts. As proposed in US3,767,667, it is prepared by reacting 2.6g of aniline hydrochloride and 1.5g of sodium azide, 5ml of triethyl orthoformate under the catalysis of 10ml of acetic acid. [0003] The three-component reaction route of amine hydrochloride, sodium azide and triethyl orthoformate has the advantages of mild reaction conditions and high yield. Compared with the previous application of isonitrile compounds and highly toxic azide Acid reactions to prepare tetrazoles have made great progress. However, this reaction route still has major disadvantages: firstly, the amine needs to be made into hydrochloride for ...

Claims

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Application Information

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IPC IPC(8): C07D257/04
Inventor 苏为科洪志
Owner ZHEJIANG UNIV OF TECH
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