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N,N-dimethylamino ethyl acrylate preparation method

A technology of ethyl dimethylaminoacrylate and ethyl formyl acetate, which is applied in the field of preparation of ethyl N,N-dimethylaminoacrylate, can solve problems such as high raw material prices, difficulty in purchasing, and viscous mother liquor, and reduce the The content of impurities, cheap and easy-to-obtain raw materials, and the effect of reducing viscosity

Inactive Publication Date: 2016-06-08
NANJING ZHUOYE PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is slightly improved on the basis of the previous two patents, but the mother liquor produced by the one-pot method is very viscous and difficult to post-process; and many by-products such as N,N-dimethylformamide and N,N- Dimethylacetamide, etc.
[0009] Preparation of N,N-dimethylaminoethyl acrylate (Tetrahedron Letters, 2004, 46 (1), 69) by reacting ethyl propiolate and benzyl dimethylamine under the catalysis of zinc bromide in acetonitrile solvent; DMF and ethyl Oxyacetylene is prepared under the catalysis of boron trifluoride to prepare N,N-dimethylaminoethyl acrylate (RecueildesTravauxChimiquesdesPays-BAS, 1966,85,929); cyanuric chloride reacts with six molecules of DMF to produce Gold's reagent, and then reacts with Ethyl acetate prepares N, N-dimethylamino ethyl acrylate (Synthetic Communications, 1982,12 (2), 939) etc. under the action of sodium alkoxide, and these operational routes all have harsh reaction time, and productive rate is low, and raw material price is high, Procurement more difficult problem, difficult to mass-produce

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0032] Step 1: Add ethyl acetate (88g, 1mol), sodium ethoxide (68g, 1mol) and 440g of mixed solvent (ethyl acetate / ethanol=1:1) into the autoclave, close the autoclave, start stirring, nitrogen replacement , and then filled with 3.0MP carbon monoxide and heated to 40°C. Under this temperature and pressure, react for 4 hours, lower the temperature, release the pressure, and discharge the material to obtain the sodium salt of the intermediate ethyl formyl acetate.

[0033] Step 2: Add the sodium salt of the intermediate formyl ethyl acetate and 176g of mixed solvent (ethyl acetate / ethanol=1:1) into the three-necked flask, start stirring, and add dimethylamine hydrochloride (82g , 1mol), the temperature was controlled at 10°C, after 4 hours of reaction, filtered, the filtrate was concentrated until solvent-free and evaporated to obtain a crude product, rectified, and 86°C (186Pa) fractions were collected to obtain 129g of a colorless liquid. The total yield 90%.

[0034] The ex...

Embodiment 2

[0040] Step 1: Add ethyl acetate (70g, 0.79mol), sodium ethoxide (652g, 0.952mol) and 210g of mixed solvent (ethyl acetate / ethanol=1.5:1) into the autoclave, close the autoclave, start stirring, Replace with nitrogen, then fill with 2.0MP carbon monoxide, and raise the temperature to 50°C. Under this temperature and pressure, react for 3 hours, lower the temperature, release the pressure, and discharge the material to obtain the sodium salt of the intermediate ethyl formyl acetate.

[0041]Step 2: Add the sodium salt of the intermediate formyl ethyl acetate and 210 g of a mixed solvent (ethyl acetate / ethanol = 1.5:1) into a three-necked flask, start stirring, and add dimethylamine hydrochloride in batches at 20°C ( 71g, 0.87mol), the temperature was controlled at 20°C, after 3 hours of reaction, filtered, the filtrate was concentrated until solvent-free and evaporated to obtain a crude product, rectified, and 86°C (186Pa) fractions were collected to obtain 102g of colorless li...

Embodiment 3

[0045] Step 1: Add ethyl acetate (90g, 1.02mol), sodium ethoxide (139g, 2mol) and 540g of mixed solvent (ethyl acetate / ethanol=2.2:1) into the autoclave, close the autoclave, start stirring, nitrogen Replacement, and then filled with 3.0MP carbon monoxide, the temperature was raised to 60°C. Under this temperature and pressure, react for 8 hours, lower the temperature, release the pressure, and discharge the material to obtain the sodium salt of the intermediate ethyl formyl acetate.

[0046] Step 2: Add the sodium salt of the intermediate formyl ethyl acetate and 450g of mixed solvent (ethyl acetate / ethanol=2.2:1) into the three-necked flask, start stirring, and add dimethylamine hydrochloride in batches at 40°C ( 128g, 1.58mol), the temperature was controlled at 40°C, after 6 hours of reaction, filtered, the filtrate was concentrated until solvent-free and evaporated to obtain a crude product, rectified, and 86°C (186Pa) fractions were collected to obtain 132g of a colorless...

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Abstract

The present invention relates to a N,N-dimethylamino ethyl acrylate preparation method, which comprises that (1) ethyl acetate and carbon monoxide are subjected to a reaction in a mixed solvent medium of ethyl acetate and ethanol under the effect of a catalyst to obtain a sodium salt of formyl ethyl acetate, wherein the catalyst is sodium methoxide or sodium ethoxide; and (2) the sodium salt of formyl ethyl acetate is added to a mixed solvent of ethyl acetate and ethanol, and then a reaction is performed with a dimethylamine salt to prepare the N,N-dimethylamino ethyl acrylate. According to the present invention, the use of the expensive and high-toxicity raw material is avoided, the process is simple, the operation is easy, the contents of various impurities are minimized through the two-step method, and the conversion rate of the main reaction is improved; and by adjusting the ratio of the mixed solvent, the viscosity of the reaction system is reduced, such that the process is easy to enlarge, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of N,N-ethyl dimethylaminoacrylate. Background technique [0002] N,N-ethyl dimethylaminoacrylate is used as an intermediate for quinolones, especially for the preparation of ciprofloxacin hydrochloride. Ciprofloxacin hydrochloride is a class of antibacterial drugs, used for genitourinary system infection and respiratory tract infection caused by sensitive bacteria, including acute attack of bronchial infection and lung infection caused by sensitive Gram-negative bacilli. Gastrointestinal infection, caused by Shigella, Salmonella, enterotoxigenic Escherichia coli, Aeromonas hydrophila, Vibrio parahaemolyticus, etc. In addition, it can treat typhoid bone and joint infection, skin and soft tissue infection, sepsis and other systemic infections. At present, ciprofloxacin hydrochloride has become a base drug, and its dosage is increasing continuously, with remarkable economic and social benefits. The present...

Claims

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Application Information

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IPC IPC(8): C07C229/30C07C227/08C07C69/732C07C67/36
Inventor 李文森
Owner NANJING ZHUOYE PHARMA CO LTD
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