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

A technology of triazole and 1H-1, which is applied in the field of preparation of 1H-1,2,3-triazole, can solve the problems of low production efficiency, production safety risks and the like, and achieves short production route and high atom utilization rate. , The effect of route economy and environmental protection

Active Publication Date: 2017-11-24
潍坊奥通药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because of the mixed system of benzene and concentrated sulfuric acid, the reaction temperature of 100°C and the reaction time of 60 hours, there are serious production safety risks and low production efficiency.

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Dissolve 80.0g of sodium nitrite (MW69.00, 1.16mol) in 250g of purified water, stir and dissolve at 30-40°C, then cool to 0-5°C to obtain an aqueous solution of sodium nitrite for use.

[0044] Add 94.5g of 1,2-diaminoethylene hydrochloride (1.00mol) into 250g of glacial acetic acid, stir to dissolve and clarify, cool down to -10~0°C, and add dropwise 330.0g of sodium nitrite solution prepared in advance , temperature control -5 ~ 5 ℃. After dropping, continue to stir and react at 0-5°C for 20 minutes, then slowly raise the temperature to 70-80°C, and keep the reaction for 1 hour.

[0045] After the reaction, concentrate under reduced pressure to recover acetic acid, then cool to 0-5°C, adjust the pH to 8-9 with 10% lye (sodium carbonate aqueous solution), then extract with 800mL dichloromethane several times, and combine the organic layers , concentrated to obtain 68g triazole crude oil.

[0046] Then transfer 68g of triazole crude oil into a 100mL roundness rectific...

Embodiment 2

[0050] Add 94.5g of 1,2-diaminoethylene hydrochloride (1.00mol) into a mixture of 100g of water and 300g of glacial acetic acid, stir to dissolve, cool down to -10~-5°C, and add in batches 85.0g sodium nitrite (MW69.00, 1.23mol), temperature control -10~0℃. After the addition is complete, continue to stir and react at -10 to -5°C for 30 minutes, then slowly raise the temperature to 40 to 50°C, and keep the reaction for 2 hours.

[0051] After the reaction is over, concentrate under reduced pressure to recover acetic acid, add 100g of water, adjust the pH to 9-10 with 10% lye, extract with 1000mL of ethyl acetate, combine the organic layers, and concentrate to obtain 69.5g of triazole crude oil .

[0052] Then transfer 69.5g of triazole crude oil into a 100mL roundness rectification flask, carry out high vacuum column rectification, collect 90~95°C fractions (absolute pressure≤5mmHg), and obtain 64.5g of colorless and transparent liquid 1H-1 , 2,3-triazole, the purity is grea...

Embodiment 3

[0054] After mixing 200g of water and 200g of glacial acetic acid, add 85.0g of sodium nitrite (MW69.00, 1.23mol) under stirring, and after dissolving and clarifying, cool to -10~-5°C. Then, 94.5 g of 1,2-diaminoethylene hydrochloride (1.00 mol) was added to the above reaction solution in small amounts and in batches, the temperature was controlled at 0-5° C., and the addition time was controlled at 0.5-1.0 h. After the addition is complete, continue to stir and react at 0-5°C for 15 minutes, then slowly raise the temperature to 50-60°C, and keep the reaction for 2 hours.

[0055] After the reaction was finished, concentrate under reduced pressure to recover acetic acid, adjust the pH to 9-10 with 10% lye, extract with 1000 mL of dichloromethane in portions, combine the organic layers, and concentrate to obtain 69.0 g of triazole crude oil.

[0056] Then transfer 69.0g of triazole crude oil into a 100mL roundness rectification flask, carry out high vacuum column rectification,...

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Abstract

The invention discloses a preparation method of 1H-1, 2, 3-triazole. The preparation method comprises the following step: performing a reaction on a compound A and sodium nitrite in a solvent I, wherein the compound A is 1,2-diamido-ethylene, 1,2-diamido-ethylene salt or a mixture of 1,2-diamido-ethylene and 1,2-diamido-ethylene salt. Compared with the prior art, the preparation method has the beneficial effects that (1) a production line is short, the conversion rate of a target product is high, the utilization ratio of atoms is high, and the atom economy is high; (2) the molar yield is high, and the total molar yield is above 90%; (3) the solvent can be recycled and reused, and the discharge amount of waste water is very small; and (4) a production process is safe and controllable.

Description

technical field [0001] The invention belongs to the technical field of preparation of intermediates of antibiotic β-lactamase inhibitors, and in particular relates to a preparation method of 1H-1,2,3-triazole. Background technique [0002] Since the invention of antibiotics, a large number of lives have been saved clinically, and great benefits have been created for human health. At the same time, with the large-scale application of antibiotics, the immunity (drug resistance) of those pathogenic bacteria to antibiotics is becoming stronger and more, resulting in the clinical elimination of a large number of antibiotic varieties, or a substantial increase in dosage. [0003] Later, scientists discovered that the key factor causing drug resistance of pathogenic bacteria is that pathogenic bacteria have evolved an enzyme that can degrade antibiotics (such as: β-lactamase), which can decompose antibiotics before antibiotics kill pathogenic bacteria, thus making antibiotics lose ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/04
CPCC07D249/04
Inventor 杨栽根晏金华魏海鹏李喜
Owner 潍坊奥通药业有限公司
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