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

A 1H-1, 1.1H-1 technology, applied in the direction of organic chemistry, can solve the problems of difficult purification, decarboxylation, large amount of wastewater, etc., to improve the safety of process operation, simple and convenient environmental protection treatment, and convenient recycling of solid waste Effect

Inactive Publication Date: 2018-12-28
SHANGHAI JINJING CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the risk of process operation is increased, and the process operation is difficult to control, the stability is poor, the product quality is not high, the purification is difficult, the amount of waste water is large, the composition is complex, and the pressure of environmental protection treatment is high. It is not suitable for industrial production.
In route (6)~(7), benzotriazole is used as raw material, and it is oxidized with potassium permanganate under neutral or acidic conditions, the reaction color is dark, and the purity of the diacid intermediate obtained is not high
In the following decarboxylation reaction, direct dry distillation or wet decarboxylation of diacid intermediates under the catalysis of copper or copper oxides, there are difficulties in decarboxylation, high temperature, easy carbonization, low product purity, low yield and other problems, resulting in The production cost is high, and it is also not suitable for industrial scale-up production
In route (8), chromic acid and concentrated sulfuric acid are used to oxidize to obtain complex salts. Under high temperature and strong acid conditions, the color of benzotriazole turns black, the reaction selectivity is poor, the yield is low, and toxic waste water containing chromium is produced. Treatment difficulty
The toxic solvent benzene is used in the decarboxylation process, and it needs to be carried out under high pressure and high temperature conditions. The operation is dangerous and requires high equipment, which is not suitable for industrial production.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 1, the preparation of acid salt (chemical formula (II) compound)

[0042] Put 36g (0.3mol) of benzotriazole, 360ml of water, and 6g (0.15mol) of sodium hydroxide into a 1L reaction flask, raise the temperature to 40°C and add 94.8g (0.6mol) of potassium permanganate in batches to control the internal temperature 40°C, after the addition is complete, keep the reaction at 40°C for 6 hours. Heat preservation ratio, heat filter to remove manganese dioxide solid, rinse with hot water, drain, cool the filtrate to 25°C, add 5% hydrochloric acid dropwise to adjust pH=2, stir for 30min, then cool to 0°C and stir for 2 hours. Suction filtration, rinse with water, and drain. Dry in a hot-air circulating oven at 70°C for 8 hours to obtain 35.63 g of off-white solid chemical formula (II), with a yield of 86%.

[0043] 2. Preparation of 1H-1,2,3-triazole (chemical formula (Ⅲ) compound)

[0044] Put 1000g of chemical formula (II) into a 3L flask, put in 2000ml of DMF, stir and rais...

Embodiment 2

[0046] 1, the preparation of acid salt (chemical formula (II) compound)

[0047]36g (0.3mol) of benzotriazole, 720ml of water, 25.2g (0.45mol) of potassium hydroxide were put into a 1L reaction flask, and 189.6g (1.2mol) of potassium permanganate was added in batches when the temperature was raised to 60°C. The temperature was 60°C, and the addition was completed, and the reaction was kept at 60°C for 3 hours. Heat preservation ratio, hot filtration to remove manganese dioxide solids, rinse with hot water, drain, cool the filtrate to 20-25°C, add concentrated sulfuric acid dropwise to adjust the pH of the solution to 2, stir for 30min, then cool to 0-5°C and stir 1 to 2 hours. Suction filtration, rinse with water, and drain. After vacuum drying at 80°C for 7 hours, 38 g of off-white solid chemical formula (II) was obtained, with a yield of 91%.

[0048] 2. Preparation of 1H-1,2,3-triazole (chemical formula (Ⅲ) compound)

[0049] Put 200g of chemical formula (II) into a 3L ...

Embodiment 3

[0051] 1, the preparation of acid salt (chemical formula (II) compound)

[0052] Put 36g (0.3mol) of benzotriazole, 1440ml of water, and 24g (0.6mol) of sodium hydroxide into a 2L reaction flask, raise the temperature to 80°C and add 284.4g (1.8mol) of potassium permanganate in batches to control the internal temperature 80°C, after the addition is complete, keep the reaction at 100°C for 1 hour. Heat preservation ratio, hot filtration to remove manganese dioxide solids, rinse with hot water, drain, cool the filtrate to 20-25°C, add 5% sulfuric acid dropwise to adjust the pH of the solution to 2, stir for 30min, then cool to 0°C and stir for 2 Hour. Suction filtration, rinse with water, and drain. After vacuum drying at 100°C for 6 hours, 38 g of off-white solid chemical formula (II) was obtained, with a yield of 91%.

[0053] 2. Preparation of 1H-1,2,3-triazole (chemical formula (Ⅲ) compound)

[0054] Put 200g of chemical formula (II) into a 3L flask, put in 2000ml of DMA...

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Abstract

The invention discloses a preparation method of 1H-1,2,3-triazole. According to the method, benzotriazole is taken as a raw material and subjected to oxidation and decarboxylation, then distillation purification is performed, and high-purity 1H-1,2,3-triazole is obtained. Raw materials of the whole synthesis route are cheap and easily available, operation is simple and convenient, operation cost is low, the process is environmentally friendly, and the method is quite suitable for industrial production and has quite high industrial application value.

Description

technical field [0001] The invention belongs to the technical field of fine chemical preparation, and in particular relates to a preparation method of 1H-1,2,3-triazole. Background technique [0002] 1H-1,2,3-Triazole is an important fine pharmaceutical chemical intermediate and an important intermediate of the β-lactamase inhibitor tazobactam, and it can also be used in other drugs or fine chemical products usage of. [0003] At present, through the retrieval of Chinese and foreign literature, the synthesis methods of 1H-1,2,3-triazole are roughly as follows: [0004] (1) The literature Cationo A, 1,2,3-Triazole [J]. Ann.chim (Rome) 1968, 58, 1507-1509 reports that it is prepared directly from azido acid and alkynes or alkenes under high temperature and high pressure conditions. [0005] (2) Patent JP06410942 synthesizes 1H-1,2,3-triazole by using the monooxime hydrazone or acyloxime hydrazone of glyoxal produced by the reaction of 1,2-dichloroacetaldehyde and urne hydroc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/04
CPCC07D249/04
Inventor 谢骏陈学军李琴唐松青
Owner SHANGHAI JINJING CHEM CO LTD
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