Method for preparing important intermediate 1H-1,2,3-triazole of Tazobactam

A technology of tazobactam and 1H-1, which is applied in the field of preparation of 1H-1,2,3-triazole, an important intermediate of tazobactam, can solve problems such as unsuitable scale-up production, harsh conditions and high price problems, to achieve broad market prospects and economic benefits, mild reaction conditions, and easy operation

Active Publication Date: 2019-09-17
山东安信制药有限公司 +1
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  • Summary
  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0019] This method requires strict temperature control, harsh conditions, and the use of special catalysts, which is expensive and expensive, and is not suitable for scale-up production

Method used

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  • Method for preparing important intermediate 1H-1,2,3-triazole of Tazobactam
  • Method for preparing important intermediate 1H-1,2,3-triazole of Tazobactam
  • Method for preparing important intermediate 1H-1,2,3-triazole of Tazobactam

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] (1) In a 500ml three-neck flask, add 100ml methanol and 100g (0.69mol) 40% glyoxal solution, stir, and cool down to -5~5°C. 240g (1.72mol) of 50% hydroxylamine hydrochloride solution was added dropwise, and a white solid was gradually precipitated in the feed solution. After dropping, heat to reflux for 2h, and the solid dissolves. Cool down to -10-0°C for crystallization for 3 hours, filter, rinse the filter cake with 20ml of cold methanol to obtain a white wet product, and vacuum-dry at 30-40°C for 5 hours. 53.9 g of a white crystalline solid was obtained, namely Intermediate 1, with a purity of 98.72% and a yield of 88.9%.

[0049] (2) In a 1000ml three-neck flask, add 300ml of methanol, 51g (0.58mol) of intermediate one, 44.2g (0.70mol) of ammonium chloride, control the temperature at 25-35°C, stir, and dissolve the solid, slowly add 110g ( 0.70mol) 35% peracetic acid, the reaction solution gradually turned dark red, after the addition was completed, the heat pres...

Embodiment 2

[0054] (1) In a 1000ml three-neck flask, add 300ml of ethanol and 200g (1.38mol) of 40% glyoxal solution, stir, and cool down to -5~5°C. 425g (3.04mol) of 50% hydroxylamine hydrochloride solution was added dropwise, and a white solid was gradually precipitated in the feed solution. After dropping, heat to reflux for 2h, and the solid dissolves. Cool down to -10-0°C for crystallization for 3 hours, filter, rinse the filter cake with 50ml of cold ethanol to obtain a white wet product, and vacuum-dry at 30-40°C for 5 hours. 105.8 g of a white crystalline solid was obtained, namely Intermediate 1, with a purity of 98.55% and a yield of 87.2%.

[0055] (2) In a 1000ml three-necked flask, add 50% 300ml acetonitrile aqueous solution, 102g (1.16mol) of intermediate one, 174g (1.32mol) of ammonium sulfate, control the temperature at 25-35°C, stir, the solid dissolves, slowly add 86.8 g (1.28mol) 50% hydrogen peroxide, the reaction solution gradually turned dark red, after the additio...

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PUM

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Abstract

The invention discloses a method for preparing an important intermediate 1H-1,2,3-triazole of Tazobactam. The method comprises the steps: firstly, subjecting glyoxal to a reaction with hydroxylamine hydrochloride, so as to obtain an intermediate I; subjecting the intermediate I and an ammonium salt to cyclization in the presence of a catalyst, so as to obtain an intermediate II; and subjecting the intermediate II to a reaction with nitrite under acidic conditions to deaminate so as to obtain crude triazole, and carrying out further refining, thereby obtaining finished triazole. According to the method, the operation is simple, the production cycle is short, the aftertreatment is simple, few waste gases, waste water and waste residues are produced, and the obtained product is high in yield, good in purity and low in cost, so that the method is more applicable to industrial large-scale production.

Description

technical field [0001] The invention relates to a preparation method of 1H-1,2,3-triazole, an important intermediate of tazobactam, and belongs to the technical field of medicine and chemical industry. Background technique [0002] 1H-1,2,3-triazole is an important intermediate for the synthesis of the β-lactam inhibitor tazobactam, and patents such as CN105085544A and CN107033161A all use 1H-1,2,3-triazole as an intermediate . 1H-1,2,3-triazole can also be used in the synthesis of other drugs. In addition, 1H-1,2,3-triazole can also be used in cleaning agents for electronic products, and is a widely used chemical substance. [0003] 1H-1,2,3-Triazole, molecular formula: C 2 h 3 N 3 , molecular weight: 69.07, CAS number: 288-36-8, the structural formula is as follows: [0004] [0005] There are many methods for preparing 1H-1,2,3-triazole reported in the literature, mainly as follows: [0006] 1. Patent document CN200710069580X: benzotriazole is used as the starti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/04
CPCC07D249/04
Inventor 彭坤杨庆坤刘瑜郑长胜李卓华
Owner 山东安信制药有限公司
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