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Preparation method of 1H-1, 2, 3-triazole

A 1H-1, triazole technology, applied in the direction of organic chemistry and the like, can solve the problems of high price, cumbersome process, unfriendly environment, etc., and achieve the effect of being beneficial to industrial production, simplifying the synthesis route, and cleaning the synthesis process

Inactive Publication Date: 2020-06-23
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Abstract
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Problems solved by technology

[0013] Different steps of this method use solvents of different polarities, and potassium permanganate is used for oxidative cyclization, which will produce solid waste residue, which is easy to generate impurities and is expensive; the third step uses potassium nitrite for deamination to generate diazonium salt , there is a risk of explosion, and this method uses a large amount of dichloromethane, which is highly toxic, the overall preparation process is cumbersome, the raw materials are expensive, unfriendly to the environment, and not conducive to industrial production

Method used

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  • Preparation method of 1H-1, 2, 3-triazole
  • Preparation method of 1H-1, 2, 3-triazole
  • Preparation method of 1H-1, 2, 3-triazole

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preparation example Construction

[0025] 1H-1,2,3-triazole C provided according to the present invention 2 h 3 N 3 The preparation method comprises the following steps:

[0026] In hydrazine hydrate N 2 h 4 ·H 2 O ethanol C 2 h 6 Add glyoxal C to the O solution 2 h 2 o 2 , carry out the reduction reaction to obtain glyoxal dihydrazone C 2 h 6 N 4 solution;

[0027] To the glyoxal dihydrazone C 2 h 6 N 4 The solution was added to hydrogen peroxide H 2 o 2 , carry out the cyclization reaction to obtain 1-amino-1,2,3-triazole C 2 h 4 N 4 solution;

[0028] To the 1-amino-1,2,3-triazole C 2 h 4 N 4 Add potassium permanganate KMnO to the solution 4 , heated for deamination reaction to obtain 1H-1,2,3-triazole C 2 h 3 N 3 solution.

[0029] Specifically, the reaction process according to the preparation method of the present invention is shown as follows:

[0030]

[0031] In the reduction reaction step, hydrazine hydrate N 2 h 4 ·H 2 O can adopt the hydrazine hydrate aqueous solu...

Embodiment 1

[0044] Add hydrazine hydrate N to the 2000ml reaction bottle 2 h 4 ·H 2 O (80%) 125.0g (2mol), ethanol C 2 h 6 O304.71g (6.61mol), add dropwise glyoxal C at 0°C 2 h 2 o 2 (40%) 145.1g (1mol), the dropping time is 60min, carries out reduction reaction 2 hours, makes glyoxal dihydrazone solution;

[0045] Add hydrogen peroxide H dropwise to the above-mentioned glyoxal dihydrazone solution 2 o 2 (30%) 147.3g (1.3mol), the dropping time is 180min, and the cyclization reaction is carried out at 5°C for 180min to obtain a 1-amino-1,2,3-triazole solution;

[0046] Add potassium permanganate KMnO to the above 1-amino-1,2,3-triazole solution 4 252.8g (1.6mol), react at 25°C for 35min to obtain 1H-1,2,3-triazole solution;

[0047] To the above 1H-1,2,3-triazole solution was added dichloromethane CH 2 Cl 2 170g (2mol) was extracted, the solvent was spin-dried, and the product was distilled at 76°C and a vacuum of 1.03KPa to obtain 48.35g of the product. Yield 70%.

Embodiment 2

[0049] Add hydrazine hydrate N to the 2000ml reaction bottle 2 h 4 ·H 2 O (80%) 187.5g (3mol), ethanol C 2 h 6 O478.83g (10.41mol), glyoxal C was added dropwise at 0°C 2 h 2 o 2 (40%) 217.65g (1.5mol), the dropping time is 120min, carries out reduction reaction 3 hours, makes glyoxal dihydrazone solution;

[0050] Add hydrogen peroxide H dropwise to the above-mentioned glyoxal dihydrazone solution 2 o 2 (30%) 238.1g (2.1mol), the dropwise addition time is 160min, and the cyclization reaction is carried out at 45°C for 120min to obtain a 1-amino-1,2,3-triazole solution;

[0051] Add potassium permanganate KMnO to the above 1-amino-1,2,3-triazole solution 4 316.2g (2mol), react at 15°C for 27min to obtain 1H-1,2,3-triazole solution;

[0052] To the above 1H-1,2,3-triazole solution was added dichloromethane CH 2 Cl 2 229.5g (2.7mol) was extracted, the solvent was spin-dried, and the product was distilled at 78°C and a vacuum of 1.03KPa to obtain 49.73g of the produc...

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Abstract

The invention provides a preparation method of 1H-1, 2, 3-triazole, which comprises the following steps: adding glyoxal into an ethanol solution of hydrazine hydrate, and carrying out reduction reaction to obtain a glyoxal dihydrazone solution; adding hydrogen peroxide into the glyoxal dihydrazone solution, carrying out a cyclization reaction to prepare a 1-amino-1, 2, 3-triazole solution; addingpotassium permanganate into the 1-amino-1, 2, 3-triazole solution, and heating to carry out a deamination reaction, so as to obtain a 1H-1, 2, 3-triazole solution. According to the method, the 1H-1, 2, 3-triazole can be prepared by a one-pot method, a solvent does not need to be added or replaced in the reaction process, nitrite and potassium permanganate which can generate solid waste are prevented from being used, and toxic substances such as toluenesulfonyl chloride and dioxane which are harmful to the environment are not used.

Description

technical field [0001] The invention relates to a method for preparing 1H-1,2,3-triazole, in particular to a method for preparing 1H-1,2,3-triazole by a "one-pot method", which belongs to the technical field of pharmaceutical synthesis. Background technique [0002] 1H-1,2,3-triazole (C 2 h 3 N 3 ) is an important organic synthesis intermediate, which can be used to synthesize various complex compounds in the fields of drugs, fungicides, etc. For example, it is one of the key intermediates in the synthesis of tazobactam. [0003] At present, the synthetic routes of 1H-1,2,3-triazole mainly include the following types: [0004] (1) Using o-phenylenediamine as a raw material, benzotriazole (2) is obtained through diazotization and ring closure reaction, and then oxidized by potassium permanganate to 1H-1,2,3-triazole- 4,5-dicarboxylic acid (3), and then catalyzed decarboxylation by copper powder in dioxane solvent to prepare 1H-1,2,3-triazole. [0005] [0006] This me...

Claims

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Application Information

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IPC IPC(8): C07D249/04
CPCC07D249/04
Inventor 孟宪强崔宝龙刘艳春张世磊
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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