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The preparation method of 3-n, n- ethyl dimethylaminoacrylate

A technology of dimethylamino ethyl acrylate and 3-N is applied in the field of preparation of 3-N,N-dimethylamino ethyl acrylate, which can solve the problems of low yield and the like, and achieve the effects of high yield and high purity

Active Publication Date: 2018-05-11
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] There are many reports on the synthesis method of 3-N, N-dimethylaminoethyl acrylate, such as foreign patents US544619, W02000000460, EP388744, US5030747, Chinese patents CN 101293850A and CN 103833565 A, all for 3-N, N-dimethyl The synthesis process of ethyl aminoacrylate has been improved, but the yield of high-purity 3-N, N-dimethylaminoethylacrylate is still relatively low by the currently disclosed preparation method

Method used

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  • The preparation method of 3-n, n- ethyl dimethylaminoacrylate

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preparation example Construction

[0020] The invention provides a preparation method of 3-N,N-dimethylaminoethyl acrylate, comprising:

[0021] The 3-N,N-dimethylaminoethyl acrylate crude product and the polymerization inhibitor are mixed and distilled under reduced pressure to obtain 3-N,N-dimethylaminoethyl acrylate;

[0022] The polymerization inhibitor is 2,6-dinitro-p-cresol, o-sec-butyl-4,6-dinitrophenol, 2,4-dimethyl-6-tert-butylphenol, 2,6- Di-tert-butyl-p-cresol, 2,2,6,6-tetramethylpiperidine nitroxide, 2,2,6,6-tetramethylpiperidone, N-methyl-2-pyrrolidone, di- Two of methylthiophenylenediamine, methanesulfonic acid, toluenesulfonic acid, xylenesulfonic acid, cumenesulfonic acid, dodecylbenzenesulfonic acid, pentadecylbenzenesulfonic acid and dinonylnaphthalenesulfonic acid species or two or more.

[0023] According to the present invention, in the present invention, the crude 3-N,N-dimethylaminoethyl acrylate is mixed with a polymerization inhibitor and distilled under reduced pressure to obtain 3-...

Embodiment 1

[0033] Measure 110g of absolute ethanol and 250g of toluene and mix them evenly in a constant pressure dropping funnel, add 360g of toluene into a 2000mL round-bottomed flask, replace the reaction flask with nitrogen and add 50g of metallic sodium into the reaction flask under nitrogen protection, and heat up. When the sodium metal is completely melted at 100°C, the mixture of toluene and ethanol is slowly added dropwise, and the dropwise addition is completed in about 0.5 hours. After the reaction, excess ethanol and toluene were distilled off to obtain a toluene solution of sodium ethoxide.

[0034] The toluene solution of sodium ethoxide prepared above was pressed into an autoclave, and 285 g of ethyl acetate and 100 g of toluene were added. Start stirring, fill the reaction kettle with carbon monoxide gas, control the temperature of the reaction kettle to 65 ℃-70 ℃, the pressure of the reaction kettle rises to 24-26 bar, the reaction is completed in about 4 hours, and the ...

Embodiment 2

[0038] Measure 110g of absolute ethanol and 250g of toluene and mix them evenly in a constant pressure dropping funnel, add 360g of toluene into a 2000mL round-bottomed flask, replace the reaction flask with nitrogen and add 48g of metallic sodium into the reaction flask under nitrogen protection, and heat up. When the sodium metal is completely melted at 100°C, the mixture of toluene and ethanol is slowly added dropwise, and the dropwise addition is completed in about 0.5 hours. After the reaction finishes, excess ethanol and toluene are distilled off to obtain a toluene solution of sodium ethoxide;

[0039] The toluene solution of sodium ethoxide prepared above was pressed into an autoclave, and 280 g of ethyl acetate and 100 g of toluene were added. Start stirring, fill the reaction kettle with carbon monoxide gas, control the temperature of the reaction kettle to 65 ℃-70 ℃, the pressure of the reaction kettle rises to 24-26 bar, the reaction is completed in about 4 hours, ...

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Abstract

The invention provides a preparation method of 3-N,N-dimethylaminoethyl acrylate. The method provided by the invention mixes the crude 3-N,N-dimethylaminoethyl acrylate and a polymerization inhibitor under reduced pressure for distillation, Obtain 3-N,N-dimethylaminoethyl acrylate; and make the polymerization inhibitor be 2,6-dinitro-p-cresol, o-sec-butyl-4,6-dinitrophenol, 2,4 -Dimethyl-6-tert-butylphenol, 2,6-di-tert-butyl-p-cresol, 2,2,6,6-tetramethylpiperidine nitroxide, 2,2,6,6-tetramethylene Two or more of methyl piperidone, N-methyl-2-pyrrolidone, dimethylthiophenylenediamine and organic sulfonic acid compound; the present invention selects specific polymerization inhibitor and 3-N, The N-dimethylaminoethyl acrylate crude product is mixed under reduced pressure for distillation, so that the 3-N,N-dimethylaminoethyl acrylate obtained by distillation has high purity and high yield.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of 3-N,N-dimethylamino ethyl acrylate. Background technique [0002] 3-N,N-Dimethylaminoethyl acrylate is an important fine chemical intermediate, specifically a key intermediate in the synthesis of quinolone antibacterial drugs. Quinolones are widely used because of their broad antibacterial spectrum, strong antibacterial activity, few adverse reactions, and can be combined with other antibiotics. They are the most widely used antibacterial drugs in clinical practice. [0003] There are many reports about the synthesis method of 3-N,N-dimethylamino ethyl acrylate, such as foreign patents US544619, WO2000000460, EP388744, US5030747, Chinese patents CN 101293850A and CN 103833565 A, all of which The synthesis process of amino ethyl acrylate has been improved, but the yield of high-purity 3-N,N-dimethylamino ethyl acrylate obtained by the currently disclosed p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/30C07C227/44C07C227/04
CPCC07C29/70C07C67/343C07C227/04C07C227/44C07C229/30C07C69/716C07C31/30
Inventor 韩福社薛李冰戚福玲王春艳刘长宝刘丽娟
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI