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High-temperature preparation method for 4'-bromomethyl-2-cyanobiphenyl based on based on N-bromosuccinimide

A technology of bromosuccinimide and bromosartan biphenyl is applied in the field of medicine and chemical industry, and 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. , to achieve the effects of excellent atomic economy, reduced safety hazards, and reduced processing difficulty

Inactive Publication Date: 2020-06-19
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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  • High-temperature preparation method for 4'-bromomethyl-2-cyanobiphenyl based on based on N-bromosuccinimide
  • High-temperature preparation method for 4'-bromomethyl-2-cyanobiphenyl based on based on N-bromosuccinimide
  • High-temperature preparation method for 4'-bromomethyl-2-cyanobiphenyl based on based on N-bromosuccinimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]A kind of high temperature bromosartan biphenyl preparation method based on N-bromosuccinimide, 11g 2-cyano-4-methylbiphenyl is dissolved in 30mL N,N-dimethylformamide, pack into syringe A tube; dissolve 9g N-bromosuccinimide in 30mL N,N-dimethylformamide, and put it 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 90°C, keep the temperature, turn on the 365nm 4000K LED light for 30 minutes, and turn on the flow reactor at the same time. After completion of the reaction, add 16g 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, put the filter cake in an oven to dry to obtain pure product The product 2-cyano-4-bromomethylbiphenyl has a purity of 91% and a yie...

Embodiment 2

[0040] A kind of high-temperature bromosartan biphenyl preparation method based on N-bromosuccinimide, 10g 2-cyano-4-methylbiphenyl is dissolved in 30mL glacial acetic acid, is packed in syringe A tube; Dissolve 8g of N-bromosuccinimide in 30mL of glacial acetic acid and put it into the B tube of the syringe. 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 95°C, keep the temperature, turn on the 365nm 4000K LED light for 30 minutes, and turn on 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...

Embodiment 3

[0042] A high-temperature bromosartan biphenyl preparation method based on N-bromosuccinimide, dissolving 11g of 2-cyano-4-methylbiphenyl in 30mL of ethyl acetate, and loading it into the A tube of the syringe; Dissolve 9 g of N-bromosuccinimide in 30 mL of ethyl acetate and fill it into syringe B. 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 75°C, keep the temperature, turn on the 365nm 4000K LED light for 30 minutes, and turn on the flow reactor at the same time. After the reaction is complete, add 15.6g 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 dry the filter cake in an oven to obtain the pure product The product 2-cyano-4-bromomethylbiphenyl has a purity of 90% and...

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Abstract

The invention discloses a high-temperature preparation method for 4'-bromomethyl-2-cyanobiphenyl based on based on N-bromosuccinimide, belonging to the technical field of pharmaceutical chemicals. Theinvention specifically discloses a method for preparing substituent-containing 4'-bromomethyl-2-cyanobiphenyl by using a flowing photochemical method. According to the method, an oxidant and a radical initiator are not needed; methyl biphenyl is used as a raw material; N-bromosuccinimide is used as a bromination reagent; ethyl acetate, glacial acetic acid or N, N-dimethylformamide is used as a solvent; and after the raw material and the bromination reagent are separately mixed with the solvent, all the materials flow into a pipeline through an injection pipe, are mixed by a mixer and then enter a constant-temperature water bath reactor for a reaction under illumination. According to the invention, the 4'-bromomethyl-2-cyanobiphenyl synthesized by the method is good in purity and high in yield; a reaction system is simple, has low toxicity and is suitable for industrial application in the field of biological medicines; and the method is applicable to an automatic continuous productionprocess, 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 industry, and in particular relates to a method for preparing high-temperature bromosartan biphenyl based on N-bromosuccinimide. 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 rebound, orthostatic hypote...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C253/34C07C255/50
CPCC07C253/30C07C253/34C07C255/50
Inventor 谢景力徐昊潘伟张俊勇
Owner JIAXING UNIV