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Preparation method of (E)-4-(imidazolyl methyl) cinnamate

A technology of imidazolyl methyl and cinnamate, applied in the direction of organic chemistry and the like, can solve the problems such as the inability to reduce the generation of impurities and the inability to effectively improve the yield, and achieve the advantages of improving convenience, improving quality and improving conversion rate. Effect

Pending Publication Date: 2021-10-12
赤峰经方医药技术开发有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This technology improves on previous methods for producing 4-(Imidazolin-2)-cinnarnates from citronic aldehydes or other starting materials through controlled chemical reactions at specific temperatures. It also reduces unwanted side products during production while maintaining high yields. Additionally, after treatments like extraction with strong bases, there's no chance of losing any more valuable compounds due to overexposure to acids. Finally, recovery processes involving evaporation allow us to make higher purity levels without adding too much salt content.

Problems solved by technology

Technological Problem addressed in this patents relating to chemical methods involves developing new or improved processes for producing certain compounds called Imidazoletanilides. These intermediary substances have potential benefits such as lower cost compared to traditional techniques like sulfuric acid salts and ammonia solutions while improving yields and quality. Additionally, they may lead to disposal issues due to their volatility during storage and transport. To address these challenges, there exists a more efficient and effective way to produce Compound Ioday Anisocyanato Acrylate.

Method used

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  • Preparation method of (E)-4-(imidazolyl methyl) cinnamate
  • Preparation method of (E)-4-(imidazolyl methyl) cinnamate
  • Preparation method of (E)-4-(imidazolyl methyl) cinnamate

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Effect test

Embodiment 1

[0037] Add 305g (4.5mol, 1.5eq) of imidazole, 180g (4.5mol, 1.5eq) of sodium hydroxide, and 1.5L of tetrahydrofuran into a 10L reaction flask, and stir at room temperature for 30min to fully react imidazole and sodium hydroxide. Cool down -5°C to 0°C and continue stirring; dissolve 765g (3.0mol, 1.0eq) of methyl 4-bromomethyl cinnamate in 3.0L tetrahydrofuran, stir to dissolve into a solution, and gradually add it dropwise to In the reaction system, after the addition is complete, keep at -5°C to 0°C to continue the reaction for 2 hours, then stop the reaction; add 3N hydrochloric acid to adjust the pH to 6-7, concentrate the reaction solution under reduced pressure, recover the solvent, pour the residue into a 20L transfer barrel, and continue Add 10 L of water, stir and crystallize, filter, and dry the filter cake at 60°C to constant weight to obtain a white solid weighing 690 g, with a yield of 95.0%. 99.52% purity.

Embodiment 2

[0039] Add 205g (3.0mol, 1.2eq) of imidazole, 185g (3.3mol, 1.3eq) of potassium hydroxide, and 1.5L of N,N-dimethylformamide into a 5L reaction flask, and stir at room temperature for 30min to make imidazole and potassium hydroxide fully responsive. Cool down to 0°C to 5°C and continue stirring; dissolve 635g (2.5mol, 1.0eq) of methyl 4-bromomethyl cinnamate in 2.0L N,N-dimethylformamide, stir to dissolve into a solution, and drop Drop the liquid funnel into the reaction system step by step. After the addition, keep the 0℃~5℃ to continue the reaction for 2h, stop the reaction; add 3N hydrochloric acid to adjust the pH to 6~7, pour the reaction solution into a 20L transfer bucket, continue to add 10L of water, and stir Crystallize, filter, and dry the filter cake at 60° C. to constant weight to obtain a white solid weighing 550 g with a yield of 91.2%. 98.88% purity.

Embodiment 3

[0041] Add 340g of imidazole (5.0mol, 2.0eq), 280g of potassium hydroxide (5.0mol, 2.0eq), 1.8L of acetonitrile into a 10L reaction flask, stir and react at room temperature for 1h, the system turns into an orange-red liquid, and control the temperature at 0°C to 5 Continue to stir the reaction for 30 min at ℃; dissolve 670 g (2.5 mol, 1.0 eq) of ethyl 4-bromomethyl cinnamate in 3.0 L of acetonitrile, stir to dissolve, and dissolve ethyl 4-bromomethyl cinnamate in batches The acetonitrile solution was gradually added dropwise into the imidazole / potassium hydroxide reaction system through the dropping funnel. After the addition was complete, the reaction was continued at 0°C to 5°C for 3 hours, and the reaction was monitored by TLC (developing solvent: ethyl acetate / isopropanol / water / ammonia water =7ml / 14ml / 5ml / 0.6ml, UV254nm) to stop the reaction until the raw materials disappear; add acetic acid to adjust the pH to 6-7, concentrate the reaction solution under reduced pressure,...

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Abstract

The invention discloses a preparation method of ozagrel sodium key intermediate (E)-4-(imidazolyl methyl) cinnamate, and belongs to the field of chemical pharmacy. The method comprises the following steps of: adding imidazole, alkali and a solvent into a reaction flask, stirring to uniformly mix the imidazole, alkali and solvent, and cooling an obtained solution ; and adding the solution of 4-bromomethyl cinnamate into the solution of imidazole and alkali, controlling the temperature to perform a reaction until the reaction is finished, adding acid to quench the reaction, adding water to crystallize, performing filtering, washing and drying to obtain the (E)-4-(imidazolyl methyl) cinnamate product. The method can greatly reduce the generation of byproducts, and improves the purity and conversion rate of the reaction.

Description

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Claims

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Application Information

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Owner 赤峰经方医药技术开发有限责任公司
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