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Method for catalytically preparing 5'-substituted tetrazole compound by zinc Lewis acid surfactant

A technique for the preparation of surfactants and catalysis, which is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc. Low activity and other problems, achieve the effect of reducing catalyst dosage and reaction time, increasing reaction rate and conversion rate, improving solubility and dispersibility

Inactive Publication Date: 2018-08-03
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

The zinc Lewis acid surfactant catalyzed by the present invention prepares the method for 5 '-substituted tetrazole compound, aims at at least to a certain extent overcoming the following deficiencies in the prior art: when using divalent zinc salt as catalyst, aftertreatment The operation is complicated, a large amount of chemical waste is produced, and the recycling of the catalyst cannot be realized, resulting in high production costs and cannot be industrialized; when zinc chloride is used as the catalyst, the solvation effect is serious, and the scope of application of the substrate is limited, while zinc bromide is used as the catalyst When the reaction activity is low, a longer reaction time and a higher reaction temperature are required

Method used

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  • Method for catalytically preparing 5'-substituted tetrazole compound by zinc Lewis acid surfactant
  • Method for catalytically preparing 5'-substituted tetrazole compound by zinc Lewis acid surfactant
  • Method for catalytically preparing 5'-substituted tetrazole compound by zinc Lewis acid surfactant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053]

[0054] A kind of preparation method of 5'-substituted tetrazole compound II-1, its steps are:

[0055] A. Add ethyl thiocyanate I-1 (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;

[0056] B. Add zinc Lewis acid surfactant Zn(OSO 2 C 10 h 21 ) 2 (0.02mol, 10.0g),;

[0057] C. stirring reaction at room temperature, the reaction time is 0.5h;

[0058] D. Add hydrobromic acid dropwise to the mixed solution obtained in step C, adjust the pH to 1-2, centrifuge at 1000-1600rpm, and separate the mixed solution into a clear solution on the upper floor and a white turbid solution on the lower floor;

[0059] E. Cool the clear solution (upper layer) separated in step D to below 5°C, and recrystallize to obtain 12.0 g of 5′-ethylthiotetrazolium compound II-1, with a yield of 92%;

[0060] F. Cool the white turbid liquid (lower layer) separated in step D to below 10°C, and r...

Embodiment 2

[0065]

[0066] A kind of preparation method of 5'-substituted tetrazole compound II-2, its steps are:

[0067] A. Add methyl thiocyanate I-2 (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;

[0068] B. Add zinc Lewis acid surfactant Zn(OSO 2 C 10 h 21 ) 2 (0.02mol, 10.0g),;

[0069] C. stirring reaction at room temperature, the reaction time is 0.5h;

[0070] D. Add hydrobromic acid dropwise to the mixed solution obtained in step C, adjust the pH to 1-2, centrifuge at 1000-1600rpm, and separate the mixed solution into a clear solution on the upper floor and a white turbid solution on the lower floor;

[0071] E. Cool the clear solution (upper layer) separated in step D to below 5°C, and recrystallize to obtain 10.2 g of 5'-methylthiotetrazolium compound II-2, with a yield of 88%;

[0072] F. Cool the white turbid liquid (lower layer) separated in step D to below 10°C, and...

Embodiment 3

[0077]

[0078] A kind of preparation method of 5'-substituted tetrazole compound II-3, its steps are:

[0079] A. Add phenyl thiocyanate I-3 (0.1mol, 13.5g), sodium azide (0.12mol, 7.8g) and water (300ml) in the reaction vessel, stir fully at room temperature to obtain a mixed solution;

[0080] B. Add zinc Lewis acid surfactant Zn(OSO 2 C 10 h 21 ) 2 (0.02mol, 10.0g),;

[0081] C. stirring reaction at room temperature, the reaction time is 0.5h;

[0082] D. Add hydrobromic acid dropwise to the mixed solution obtained in step C, adjust the pH to 1-2, centrifuge at 1000-1600rpm, and separate the mixed solution into a clear solution on the upper floor and a white turbid solution on the lower floor;

[0083] E. Cool the clear solution (upper layer) separated in step D to below 5°C, and recrystallize to obtain 16.9 g of 5′-phenylthiotetrazolium compound II-3, with a yield of 95%;

[0084] F. Cool the white turbid liquid (lower layer) separated in step D to below 10°C, an...

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Abstract

The invention belongs to the technical field of organic synthesis and in particular relates to a method for preparing a 5'-substituted tetrazole compound by taking a zinc Lewis acid surfactant as a catalyst. The method comprises the following steps: 1) taking the zinc Lewis acid surfactant Zn(OSO2CnH2n+1)2 as the catalyst and enabling R group nitrile and sodium azide to react in water, so as to obtain zinc salt of a 5'-R group tetrazole compound and a byproduct NaOSO2CnH2n+1; 2) acidifying the zinc salt of the 5'-R group tetrazole compound obtained by step 1) under an acidic condition to obtain the 5'-R group tetrazole compound and a byproduct zinc bromide; 3) carrying out substitution reaction on the byproduct NaOSO2CnH2n+1 and the byproduct zinc bromide under an acidic condition to obtain the zinc Lewis acid surfactant Zn(OSO2CnH2n+1)2. In the method, a one-pot-method strategy can be adopted and starting raw materials are subjected to continuous cyclization reaction and acidification reaction to directly prepare a target compound containing a tetrazole structure unit; the zinc Lewis acid surfactant used in the method can be recycled after the reaction is finished.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing 5'-substituted tetrazole compounds by using a zinc Lewis acid surfactant as a catalyst. Background technique [0002] 5′-substituted tetrazole compounds have very important applications in the fields of biochemistry, pharmaceutical industry and fine chemical industry, and their structures widely exist in drug molecules and intermediates, such as losartan, candesartan, etc. for the treatment of hypertension Drugs for diabetes, diabetes and congestive heart failure all contain tetrazolium structures. In addition, 5′-substituted tetrazole compounds can also be used in the synthesis of a new generation of cephalosporin antibiotics and intermediates in the synthesis of antifungal drugs. Stability during storage. Therefore, the efficient synthesis of 5′-substituted tetrazole compounds has attracted extensive attention in recent years. Mos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/04B01J31/02
CPCB01J31/0225C07D257/04
Inventor 李清平徐志丹
Owner 湖北佰智昂生物化工有限公司
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