Method for preparing 1H-1,2,3-triazole

A 1H-1, triazole technology, applied in the field of medicine and chemical industry, can solve the problems of high price, difficult to buy starting materials, unsuitable for industrialized large-scale production, etc., achieves simple operation, safe and environmentally friendly synthesis process, broad market prospects and economic effect

Active Publication Date: 2019-03-29
山东安信制药有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0025] The starting material of this method is not easy to purchase, the price

Method used

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  • Method for preparing 1H-1,2,3-triazole
  • Method for preparing 1H-1,2,3-triazole
  • Method for preparing 1H-1,2,3-triazole

Examples

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Effect test

Embodiment example 1

[0048] In a 500ml three-necked flask, add 150ml water, 107.5g (1.72mol) 80% hydrazine hydrate solution, stir, and cool to -5~5°C. 100g (0.69mol) of 40% glyoxal solution was added dropwise, and a white solid gradually precipitated in the feed solution. After dripping, react at room temperature for 2h. Crystallize at a temperature below 0°C for 3h, filter, rinse the filter cake with 30ml of cold methanol to obtain a white wet product, and vacuum dry at 30-40°C for 5h. 54.2 g of white crystalline solid was obtained, with a yield of 91.3%, which is the intermediate one.

[0049] In a 1000ml three-necked flask, add 300ml of dichloromethane, 50.0g (0.58mol) of Intermediate One, control the temperature at 25~35℃, stir until the material liquid is clear, add 110g (0.70mol) potassium permanganate in 5 times to react The liquid gradually turned dark red. After the addition, the reaction was kept for 3 hours. After the reaction was completed, a light red filtrate was obtained by filtratio...

Embodiment example 2

[0053] In a 2000ml three-necked flask, add 750ml of water and 538.0g (8.61mol) of 80% hydrazine hydrate solution, stir and cool to -5~5°C. 500.0g (3.45mol) of 40% glyoxal solution was added dropwise, and a white solid gradually precipitated in the feed liquid. After dripping, react at room temperature for 2h. Crystallize at a temperature below 0°C for 3h, filter, and rinse the filter cake with 150ml of cold methanol to obtain a white wet product, which is dried under vacuum at 30-40°C for 5h. 273.2 g of a white crystalline solid was obtained with a yield of 92.1%, which is the intermediate one.

[0054] In a 3000ml three-necked flask, add 1620ml of dichloromethane, 270.0g (3.13mol) of Intermediate One, control the temperature at 25~35℃, stir until the material liquid is clear, add 595.0g (3.76mol) potassium permanganate in 5 times, The reaction solution gradually turned dark red. After the addition, the reaction was kept for 3 hours. After the reaction was completed, a light re...

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Abstract

The invention discloses a method for preparing 1H-1,2,3-triazole. The method comprises the following steps of: in a polar solvent, reacting glyoxal and hydrazine hydrate to obtain an intermediate 1, and then performing cyclization under the action of potassium permanganate to obtain an intermediate 2, reacting the intermediate 2 and potassium nitrite under acidic conditions for deamination to obtain a crude product triazole, and further purifying the crude product to obtain the finished product triazole. The method has the advantages of simple operation, short production cycle, and simple post-treatment, and the product has high yield, good purity and low cost, and is more suitable for industrial large-scale production.

Description

Technical field [0001] The invention relates to a preparation method of 1H-1,2,3-triazole, which belongs to the technical field of medicine and chemical industry. Background technique [0002] 1H-1,2,3-triazole, molecular formula: C 2 H 3 N 3 , Molecular weight: 69.07, CAS number: 288-36-8, structural formula is as follows: [0003] [0004] 1H-1,2,3-triazole is an important intermediate for the synthesis of the new β-lactam inhibitor tazobactam, and 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 it is a widely used chemical substance. [0005] The current methods for preparing 1H-1,2,3-triazole mainly include the following: [0006] (1) Patent document CN200710069580X: Using benzotriazole as starting material, 4,5-dicarboxytriazole is obtained by oxidation and ring opening of potassium permanganate, and then decarboxylated at high temperature under the action of catalyst to obtain crud...

Claims

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Application Information

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IPC IPC(8): C07D249/04
CPCC07D249/04
Inventor 彭坤杨庆坤李卓华张重坤
Owner 山东安信制药有限公司
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