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Normal-temperature 4'-bromomethyl-2-cyanobiphenyl preparation method based on sodium bromide-sodium bromate system

A technology of bromosartan biphenyl and sodium bromate, which is applied in the field of medicine and chemical industry, can solve the problems of inability to apply continuous and semi-continuous automatic production lines, increase the pressure of wastewater treatment, and increase the pressure of environmental protection treatment, etc., and achieve atomic Excellent economy, reduced energy consumption, and shortened response time

Inactive Publication Date: 2020-06-26
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned preparation method still needs hydrogen peroxide as an oxidizing agent, and N-hydroxyphthalimide etc. as a free radical initiator. Handling pressure, not suitable for actual production application
[0006] In particular, the preparation methods of the above-mentioned 2-cyano-4'-bromomethylbiphenyl all use auxiliary agents such as oxidants and free radical initiators, which increase the preparation cost while also increasing the environmental protection treatment pressure, and , the above-mentioned method has a long preparation cycle and a large feeding ratio, and cannot be applied to the technological change trend of continuous and semi-continuous automatic production lines in actual industrial production.

Method used

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  • Normal-temperature 4'-bromomethyl-2-cyanobiphenyl preparation method based on sodium bromide-sodium bromate system
  • Normal-temperature 4'-bromomethyl-2-cyanobiphenyl preparation method based on sodium bromide-sodium bromate system
  • Normal-temperature 4'-bromomethyl-2-cyanobiphenyl preparation method based on sodium bromide-sodium bromate system

Examples

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Effect test

Embodiment 1

[0038]A kind of normal temperature bromosartan biphenyl preparation method based on sodium bromide-sodium bromate system, 10g 2-cyano-4-methylbiphenyl is dissolved in 30mL acetone, puts into syringe A tube; Sodium bromide and 3g of sodium bromate were dissolved in 30mL of acetone and put into syringe B tube. Install the two syringes A and B on the flow syringe pump, assemble them, and set the flow rate of both tubes A and B to 1.5mL / min. Turn on the constant temperature water bath device, heat to 55°C, keep the temperature, turn on the 365nm 4000KLED light for 30 minutes, and open the flow reactor at the same time. After completion of the reaction, add 15 g of sodium bisulfite to the received product to quench, separate the liquids, remove the solvent by rotary evaporation of the organic phase, add isopropyl ether for recrystallization, filter with suction, and put the filter cake in an oven to dry to obtain pure product The product 2-cyano-4-bromomethylbiphenyl has a purity ...

Embodiment 2

[0040] A kind of normal temperature bromosartan biphenyl preparation method based on sodium bromide-sodium bromate system, 10g 2-cyano-4-methylbiphenyl is dissolved in 30mL acetone, puts into syringe A tube; Sodium bromide and 3g of sodium bromate were dissolved in 30mL of acetone and put into syringe B tube. Install the two syringes A and B on the flow syringe pump, assemble them, and set the flow rate of both tubes A and B to 1.5mL / min. Turn on the constant temperature water bath device, heat to 30°C, keep the temperature, turn on the 385nm 4000KLED light for 30 minutes, and open the flow reactor at the same time. After completion of the reaction, add 15 g of sodium bisulfite to the received product to quench, separate the liquids, remove the solvent by rotary evaporation of the organic phase, add isopropyl ether for recrystallization, filter with suction, and put the filter cake in an oven to dry to obtain pure product The product 2-cyano-4-bromomethylbiphenyl has a purity...

Embodiment 3

[0042] A kind of normal temperature bromosartan biphenyl preparation method based on sodium bromide-sodium bromate system, 10g 2-cyano-4-methylbiphenyl is dissolved in 30mL acetone, puts into syringe A tube; Sodium bromide and 3g of sodium bromate were dissolved in 30mL of acetone and put into syringe B tube. Install the two syringes A and B on the flow syringe pump, assemble them, and set the flow rate of both tubes A and B to 1.5mL / min. Turn on the constant temperature water bath device, heat to 60°C, keep the temperature, turn on the 4000K LED light of 405nm for 30 minutes, and open the flow reactor at the same time. After completion of the reaction, add 15 g of sodium bisulfite to the received product to quench, separate the liquids, remove the solvent by rotary evaporation of the organic phase, add isopropyl ether for recrystallization, filter with suction, and put the filter cake in an oven to dry to obtain pure product The product 2-cyano-4-bromomethylbiphenyl has a pu...

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Abstract

The invention discloses a normal-temperature 4'-bromomethyl-2-cyanobiphenyl preparation method based on a sodium bromide-sodium bromate system, belongs to the technical field of pharmaceutical chemicals, and particularly discloses a method for preparing substituent-containing 4'-bromomethyl-2-cyanobiphenyl by using a flowing photochemical method. An oxidant and a radical initiator are not needed;and methyl biphenyl is used as a raw material, sodium bromide and sodium bromate are used as bromination reagents, acetone, dichloromethane, petroleum ether or acetonitrile is used as a solvent, and after the raw material and the bromination reagents are respectively mixed with the solvent, the obtained mixtures flow into a pipeline through injection pipes, and are mixed by a mixer, and then the obtained mixture enters a constant-temperature water bath reactor and is subjected to a reaction through illumination. The 4'-bromomethyl-2-cyanobiphenyl synthesized by the preparation method is good in purity, high in yield, simple in reaction system and low in toxicity, is suitable for industrial application in the field of biological medicines, can be suitable for an automatic continuous production process, and conforms to the development concepts of green chemical industry, high efficiency and economy.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical engineering, and in particular relates to a method for preparing bromosartan biphenyl at room temperature based on a sodium bromide-sodium bromate system. Background technique [0002] Sartan drugs are the first-line antihypertensive drugs, with a brand-new antihypertensive mechanism, stable antihypertensive, good curative effect, long duration of action, and good patient tolerance. Angiotensin II receptor antagonist (ARB) antihypertensive drugs ("sartan" drugs) have been available for more than 20 years, because of their obvious antihypertensive effect and good tolerance, especially the clinical trial data show that they have antihypertensive effects on the heart. The unique curative effect and protective effect on vascular diseases have become one of the most common antihypertensive drugs in clinical practice. The incidence of adverse reactions such as dry cough, drug withdrawal r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/50
CPCC07C253/30C07C255/50
Inventor 谢景力徐昊潘伟张俊勇
Owner JIAXING UNIV