Preparation method of normal-temperature bromoethyl cyanobiphenyl based on dibromohydantoin

A technology of bromosartan biphenyl and dibromohydantoin, 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 environmental protection treatment, increase the pressure of waste water treatment, etc. Excellent atomic economy, shortened reaction time, and reduced energy consumption

Inactive Publication Date: 2020-06-23
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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  • Preparation method of normal-temperature bromoethyl cyanobiphenyl based on dibromohydantoin

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Effect test

Embodiment 1

[0038] A method for preparing bromosartan biphenyl at room temperature based on dibromohydantoin, 10g of 2-cyano-4-methylbiphenyl is dissolved in 30mL of acetone, and put into syringe A tube; 9g of dibromohydantoin Dissolve in 30mL acetone 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 55°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 purity of 91% and a yield of 90%.

Embodiment 2

[0040] A method for preparing bromosartan biphenyl at room temperature based on dibromohydantoin, 10g of 2-cyano-4-methylbiphenyl is dissolved in 30mL of acetone, and put into syringe A tube; 9g of dibromohydantoin Dissolve in 30mL acetone 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 30°C, keep the temperature, turn on the 385nm 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 purity of 90% and a yield of 93%.

Embodiment 3

[0042] A method for preparing bromosartan biphenyl at room temperature based on dibromohydantoin, 10g of 2-cyano-4-methylbiphenyl is dissolved in 30mL of acetone, and put into syringe A tube; 9g of dibromohydantoin Dissolve in 30mL acetone 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 60°C, keep the temperature, turn on the 4000K LED light of 405nm 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 purity of 91% and a yield of 92%.

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Abstract

The invention discloses a preparation method of normal-temperature bromoethyl cyanobiphenyl based on dibromohydantoin, and belongs to the technical field of pharmaceutical chemicals, and particularlydiscloses a method for preparing substituent-containing bromoethyl 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, dibromohydantoin is used as a bromination reagent, acetone, dichloromethane, petroleum ether or acetonitrile is used as a solvent, and after the raw material and the bromination reagent are respectively mixed with the solvent, the mixture flows into a pipeline through an injection pipe, is mixed by a mixer, then enters a constant-temperature water bath reactor and is subjected to a reaction through illumination. The 2-cyano-4 '-bromomethylbiphenyl synthesized by the 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 chemicalindustry, 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 bromosartan biphenyl at room temperature based on dibromohydantoin. 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 hypot...

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
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