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Synthesis method for preparing 1H-1, 2, 3-triazole by continuous flow

A synthesis method and 1H-1 technology, applied in organic chemistry and other directions, can solve the problems of high safety risk and low production efficiency, and achieve the effect of reducing safety risk, good product quality and improving catalyst utilization rate.

Pending Publication Date: 2021-12-31
SHANGHAI HAOYUAN CHEMEXPRESS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] In view of the above technical background, in order to solve the problems of high safety risk and low production efficiency in the kettle process in the prior art

Method used

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  • Synthesis method for preparing 1H-1, 2, 3-triazole by continuous flow
  • Synthesis method for preparing 1H-1, 2, 3-triazole by continuous flow
  • Synthesis method for preparing 1H-1, 2, 3-triazole by continuous flow

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Embodiment 1

[0042] This embodiment provides a preparation method of 1H-1,2,3-triazole, which specifically includes the following steps:

[0043] 1) Take 91.2g of 80% hydrazine hydrate solution and pump it into the preheating equipment at a flow rate of 0.5mL / min for preheating. The preheating temperature is 35°C. 100g of aqueous solution is pumped into the reactor at a flow rate of 0.5mL / min, the temperature of the reactor is set at 30°C, and then the two react, and the intermediate I is collected through the condenser at room temperature;

[0044] 2) Add 1000mL ethanol to intermediate I and mix it evenly, pump it into the reaction column tube containing manganese dioxide (1.0 equivalent) at a flow rate of 0.5mL / min, and inject oxygen into it at a speed of 10mL / min Carry out the oxidation reaction in the above-mentioned continuous reaction column, and the reaction temperature is set at 25° C. to obtain intermediate II;

[0045] 3) Put the obtained intermediate II and 30% hydrochloric aci...

Embodiment 2

[0048] This embodiment provides a preparation method of 1H-1,2,3-triazole, which specifically includes the following steps:

[0049] 1) Take 91.2g of 80% hydrazine hydrate solution and pump it into the preheating equipment at a flow rate of 1mL / min for preheating. The preheating temperature is 40°C. 100g was pumped into the reactor at a flow rate of 0.5mL / min, and the temperature of the reactor was set at 40°C, and then the two reacted, and the intermediate I was collected by cooling down to room temperature through the condenser;

[0050] 2) Add 1000mL of ethanol to Intermediate I and mix it evenly, pump it into the reaction column tube containing manganese dioxide (1.0 equivalent) at a flow rate of 1mL / min, inject oxygen into the reaction column at a rate of 20mL / min Oxidation reaction is carried out in the above-mentioned continuous reaction column, and the reaction temperature is set at 25° C. to obtain intermediate II;

[0051] 3) Put intermediate II and 30% hydrochloric...

Embodiment 3

[0054] This embodiment provides a preparation method of 1H-1,2,3-triazole, which specifically includes the following steps:

[0055] 1) Take 91.2g of 80% hydrazine hydrate solution and pump it into the preheating equipment at a flow rate of 1mL / min for preheating. The preheating temperature is 60°C. 100g was pumped into the reactor at a flow rate of 1mL / min, and the temperature of the reactor was set at 60°C, and then the two reacted, and the intermediate I was collected by cooling down to room temperature through the condenser;

[0056] 2) Add 1000mL ethanol to Intermediate I and mix it evenly, pump it into the reaction column tube containing manganese dioxide (1.0 equivalent) at a flow rate of 1mL / min, inject oxygen into the reaction column at a rate of 30mL / min Oxidation reaction is carried out in the above-mentioned continuous reaction column, and the reaction temperature is set at 35° C. to obtain intermediate II;

[0057] 3) Put intermediate II and 30% hydrochloric acid...

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Abstract

The invention discloses a synthesis method for preparing 1H-1, 2, 3-triazole by continuous flow, the reaction formula is as follows: the method comprises the following steps: step 1, in a solvent-free system and at a certain temperature, introducing hydrazine hydrate and glyoxal for reaction to obtain an intermediate I; 2, introducing a proper amount of ethanol into the intermediate I to obtain an ethanol solution of the intermediate I, introducing oxygen under the action of a manganese dioxide MnO2 catalyst, and carrying out an oxidative cyclization reaction to obtain an intermediate II; 3, the intermediate II and sodium nitrite are subjected to a diazotization reaction under the acidic condition, and 1H-1, 2, 3-triazole is obtained; and the 1H-1, 2, 3-triazole can be selectively subjected to further post-treatment to obtain the high-purity 1H-1, 2, 3-triazole. The synthesis method for preparing 1H-1, 2, 3-triazole by the continuous flow is a continuous synthesis method through the continuous flow microreactor, and the method is safe and controllable, small in hazardous waste generation amount, high in product yield and good in product quality.

Description

technical field [0001] The invention relates to a method for preparing 1H-1,2,3-triazole by continuous flow synthesis, and belongs to the technical field of drug synthesis. Background technique [0002] 1H-1,2,3-triazole (1,2,3-1H-Triazole), its chemical structure is shown in formula (1): [0003] [0004] 1H-1,2,3-Triazole is an important intermediate for the synthesis of new-type β-lactamase inhibitor tazobactam, and it is also an important intermediate for the synthesis of drugs and fungicides. [0005] At present, there are many reports on the synthesis route of 1H-1,2,3-triazole. CN109535089B discloses a preparation method of 1H-1,2,3-triazole. The method is to react glyoxal with hydrazine hydrate in a polar solvent to obtain intermediate one, then cyclize under the action of potassium permanganate to obtain intermediate II, and react intermediate two with potassium nitrite under acidic conditions for deamination The crude product of triazole was obtained, and the ...

Claims

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Application Information

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IPC IPC(8): C07D249/04
CPCC07D249/04
Inventor 曹铭张焕成王雪莲金飞敏杨绍波高强郑保富
Owner SHANGHAI HAOYUAN CHEMEXPRESS
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