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Synthesizing method of 3-N,N-dimethylamino ethyl acrylate

A technology of ethyl dimethylamino acrylate and a synthesis method, applied in the field of 3-N, can solve the problems of unsatisfactory product purity and yield, influence of high-purity product yield, incomplete reaction, etc., and achieves improvement of raw material conversion rate , the effect of easy large-scale processing and manufacturing, reducing the discharge of three wastes

Active Publication Date: 2016-07-06
SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But method (9) uses " one pot method ", because dimethylamine is introduced in the reaction system prematurely, will cause impurity to increase, in order to obtain high-purity product, need to increase rectifying column tray number, improve equipment preparation, and Finally, it has an impact on the yield of high-purity products
The "one-pot method" includes two-step reactions at the same time, and the water produced in the second step reaction will inhibit the first step reaction, making the reaction incomplete and reducing the yield, so the purity and yield of the product are not ideal

Method used

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  • Synthesizing method of 3-N,N-dimethylamino ethyl acrylate
  • Synthesizing method of 3-N,N-dimethylamino ethyl acrylate
  • Synthesizing method of 3-N,N-dimethylamino ethyl acrylate

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Effect test

Embodiment 1

[0049] S1, intermediate preparation reaction step: add 300mL toluene and 14g metallic sodium into a 500mL reaction bottle, and heat to melt. Stirring was started, and 40 g of ethanol was added dropwise. After the dropwise addition was completed, reflux was stirred for 1 hour, and the temperature was lowered to obtain a suspension of sodium ethoxide in toluene.

[0050] S2, condensation reaction step: transfer the above-mentioned sodium ethoxide toluene suspension into a 1L autoclave, add 80g ethyl acetate and 1.5g Raney nickel, close the autoclave, and start stirring; the autoclave is replaced with carbon monoxide gas after nitrogen replacement, and The pressure rises to 3-5MPa, heats to 60-70°C, stirs for 6 hours, cools down and releases the pressure.

[0051] S3, amine substitution reaction step: add 210 g of 35% dimethylamine hydrochloride aqueous solution into a 1L reaction bottle, start stirring, add the condensation reaction solution in batches at room temperature, conti...

Embodiment 2

[0054] S1, intermediate preparation step: directly add 75 g of commercially available potassium tert-butoxide solid to the toluene suspension to form an intermediate.

[0055] S2, condensation reaction step: move the above-mentioned intermediate into a 1L autoclave, add 60g of ethyl acetate and 2g of cobalt carbonyl, put together the kettle, and start stirring; the autoclave is replaced with nitrogen and then replaced with carbon monoxide gas, and the pressure rises to 1.5-2.5 MPa, heat to 80-90°C, stir for 6 hours, cool down and release the pressure.

[0056] S3, amine substitution reaction step: Add 170 g of 45% dimethylamine hydrochloride aqueous solution into a 1L reaction bottle, start stirring, add the condensation reaction solution in batches at room temperature, and continue stirring for 2 hours after the addition is complete. Then stop stirring, filter with suction, separate the layers of the filtrate, concentrate the organic phase, and rectify to obtain 3-N,N-ethyl d...

Embodiment 3

[0058] S1, intermediate preparation steps: add 200mL ethanol to a 500mL reaction bottle, add sodium metal in batches, continue stirring until the sodium metal is completely reacted after the addition, and lower the temperature to obtain a sodium ethoxide ethanol suspension.

[0059] S2, condensation reaction step: transfer the above-mentioned sodium ethoxide ethanol suspension into a 1L autoclave, add 60g of ethyl acetate and 1g of rhodium chloride, combine the kettle, and start stirring; the autoclave is replaced with carbon monoxide gas after nitrogen replacement, and pressure Rise to 4-5MPa, heat to 70-80°C, stir for 4 hours (cool down, release pressure.

[0060] S3, amine substitution reaction step: add 300 g of 20% dimethylamine hydrochloride aqueous solution into a 1L reaction bottle, start stirring, add the condensation reaction solution in batches at room temperature, continue stirring for 2 hours after the addition, and then stop stirring, After suction filtration, th...

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Abstract

The invention discloses a method for preparing 3-N,N-dimethylamino ethyl acrylate from a transition metal carbonyl complex.The method comprises the steps that a specified amount of alkali metal alkoxide and alcohol-containing organic solvent or alkali metal and / or alkali metal hydride and the alcohol-containing organic solvent are taken as raw materials to react to generate an intermediate; a condensation reaction is performed for 4-10 h in a high-pressure reaction kettle by taking the intermediate, ethyl acetate and carbon monoxide gas or ethyl formate as raw material and taking a specified substance containing a transition metal element as a catalyst under the pressure of 2-5 MPa at the temperature of 50 DEG C-100 DEG C to generate a solution containing a specified alkali metal salt; the solution is added into an aqueous dimethylamine hydrochloride solution in batches to obtain 3-N,N-dimethylamino ethyl acrylate.According to the method, by adding the transition metal element, the raw material conversion rate and the product yield are increased, the product purity is improved, the economic benefit is increased, the raw materials are easy to obtain, the atom economy is good, and the raw material utilization rate is high; part of the original auxiliary materials are recycled and reused, and therefore discharge of three wastes is greatly reduced.

Description

technical field [0001] The invention relates to the field of medical materials, in particular to a synthesis method of ethyl 3-N,N-dimethylaminoacrylate. Background technique [0002] 3-N, N-ethyl dimethylaminoacrylate is a key intermediate in the synthesis of the main ring of quinolones, and has a large market demand. The structure of quinolones is as follows: [0003] [0004] Among them, the carboxyl group at the 3-position and the oxygen at the 4-position are essential groups, and a ring can be formed between the 1-position and the 8-position. Quinolones antibacterial drugs have the advantages of broad antibacterial spectrum, strong antibacterial activity, convenient administration, less toxic and side effects, and no cross-resistance with other antibiotics. Antimicrobials. [0005] The method of synthesizing the parent ring of quinolones mainly adopts intramolecular nucleophilic substitution reaction. Condensation reaction of acid chloride or substituted aromatic...

Claims

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Application Information

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IPC IPC(8): C07C229/30C07C227/06
CPCC07C29/70C07C67/36C07C227/06C07C229/30C07C69/732C07C31/30
Inventor 黄忠林孙思曾淼徐剑锋徐志庆
Owner SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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