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The preparation method of 1-amino-1,2,3-triazole

A technology of amino and solution, applied in the direction of organic chemistry, etc., can solve the problems of cumbersome procedures, high toxicity, and easy generation of impurities, etc., and achieve the effect of clean synthesis process, less oxidation impurities, and high oxidation efficiency

Active Publication Date: 2022-03-11
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] 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, and this method uses a large amount of methylene chloride, which is highly toxic and the overall preparation The process is cumbersome, the raw materials are expensive, unfriendly to the environment, and not conducive to industrial production

Method used

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  • The preparation method of 1-amino-1,2,3-triazole
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  • The preparation method of 1-amino-1,2,3-triazole

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Embodiment 1

[0035] Add hydrazine hydrate N to the 2000mL reaction flask 2 h 4 ·H 2 O (80%) 125.0g (2mol), add glyoxal C dropwise 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;

[0036] In the above-mentioned glyoxal dihydrazone solution, pass into ozone (O 3 ) concentration is 127g / m 3 , the aeration time is 240min, and ozone (O 3 ) 62.4g, cyclization reaction at 5°C for 180min to obtain 1-amino-1,2,3-triazole solution;

[0037] The 1-amino-1,2,3-triazole solution was concentrated at 76° C. under a vacuum of 1.03 kPa to obtain 58.80 g of the product, with a yield of 70% and a purity of 99.3%.

Embodiment 2

[0039] Add hydrazine hydrate N to the 2000mL reaction flask 2 h 4 ·H 2 O (80%) 187.5g (3mol), 0 ℃ drop glyoxal 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;

[0040] In the above-mentioned glyoxal dihydrazone solution, pass into ozone (O 3 ) concentration is 130g / m 3 , the aeration time is 360min, and ozone (O 3 ) 100.8g, cyclization reaction at 45°C for 120min to prepare 1-amino-1,2,3-triazole solution;

[0041] The 1-amino-1,2,3-triazole solution was concentrated at 78°C under a vacuum of 1.03kPa to obtain 90.72g of the product, with a yield of 72% and a purity of 99.4%.

Embodiment 3

[0043] Add hydrazine hydrate N to the 2000mL reaction flask 2 h 4 ·H 2 O (80%) 162.5g (2.6mol), add glyoxal C dropwise at 0°C 2 h 2 o 2 (40%) 188.5g (1.3mol), dropwise time is 170min, carries out reduction reaction 1 hour, makes glyoxal dihydrazone solution;

[0044] In the above-mentioned glyoxal dihydrazone solution, pass into ozone (O 3 ) concentration is 129g / m 3 , the aeration time is 340min, and ozone (O 3 ) 93.6g, cyclization reaction at 25°C for 180min to prepare 1-amino-1,2,3-triazole solution;

[0045] The 1-amino-1,2,3-triazole solution was concentrated at 80° C. under a vacuum of 1.03 kPa to obtain 81.90 g of the product, with a yield of 75% and a purity of 99.3%.

[0046]1 H-NMR (DMSO-d6, 400MHz) δ (ppm): 7.87 (d, J = 8.2Hz, 1H), 7.56 (d, J = 8.2Hz, 1H), 6.85 (br s, 2H); LCMS (ES ,m / z):85[M + H] + .

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Abstract

The invention relates to a preparation method of 1-amino-1,2,3-triazole, which belongs to the technical field of pharmaceutical synthesis. The method comprises the following steps: (1) adding glyoxal to hydrazine hydrate to carry out a reduction reaction to obtain a glyoxal dihydrazone solution; (2) passing ozone into the glyoxal dihydrazone solution to carry out a cyclization reaction to obtain 1-amino-1,2,3-triazole solution; (3) concentrating and filtering to obtain 1-amino-1,2,3-triazole solid. The present invention adopts a "one-pot method". By selecting ozone as a catalyst for oxidation and forming rings, and water as a solvent, there is no need to replace or add solvents, avoiding the use of toxic initial reactants, and generating no solid waste.

Description

technical field [0001] The invention relates to a preparation method of 1-amino-1,2,3-triazole, which belongs to the technical field of pharmaceutical synthesis. Background technique [0002] 1-amino-1,2,3-triazole (C 2 h 4 N 4 ) 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 1-amino-1,2,3-triazole mainly include the following types: [0004] (1) Chinese patent CN 1136809A discloses that in water, glyoxal and hydrazine hydrate are reacted to form intermediate one, the solvent is evaporated under reduced pressure, extracted with ethyl acetate, the solvent is evaporated, and then transition metal is added under water as the solvent The oxide and hydrogen peroxide were reacted, the insoluble matter was removed by filtration, and the solvent was distille...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/04
CPCC07D249/04
Inventor 董维超崔宝龙孙铎
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD