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Method for preparing 3-N,N-dimethylamino-ethyl acrylate

A technology of dimethylamino ethyl acrylate and diethyl malonate, which is applied in the field of preparing 3-N, can solve the problems of high cost of raw materials, unsuitable for industrialization, long time, etc., and achieves that the preparation process is simple, feasible and easy to use. The effect of large-scale production and low production cost

Active Publication Date: 2008-10-29
SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method using tert-tert-butoxy-2-dimethylaminomethane and ethyl acetate as raw materials has high temperature and long time, high raw material cost and high energy consumption
The method disclosed in WO2000000460 requires a two-step reaction, and ethyl malonate monopotassium salt must first be produced. This process is difficult to control, and highly toxic dimethyl sulfate is used as a raw material, which has poor safety.
[0004] In summary, the current preparation method of 3-N,N ethyl dimethylaminoacrylate has defects no matter in the raw materials used or the specific operating conditions, and is not suitable for industrialization

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 120.6g (1.65mol) of DMF into a 2000ml four-necked flask, raise the temperature to 80°C, slowly add 231.3g (1.5mol) of diethyl sulfate, control the temperature at 80-90°C, keep it warm for 2 hours after the addition, and the reaction is over Afterwards, cool down to room temperature.

[0025] Add 900 ml of toluene, 240.2 g (1.5 mol) of diethyl malonate, and 118.6 g (1.5 mol) of pyridine into the flask, heat up to reflux, and keep the temperature for 5 hours for reaction; after the reaction, cool down to 10-20°C and filter; After the filtrate was washed three times with 500ml of water, the organic layer was collected and concentrated under reduced pressure to recover the solvent. The temperature of the concentrated under reduced pressure was 60°C, and the gauge pressure was -0.098MPa; then, the vacuum distillation was carried out, and the temperature of the reduced pressure distillation was 90 to 100°C. The vacuum degree is above 5mmHg, and 154.6g of fractions at 80-8...

Embodiment 2

[0027] Add 131.6g (1.8mol) of DMF into a 2000ml four-necked flask, raise the temperature to 80°C, slowly add 231.3g (1.5mol) of diethyl sulfate, control the temperature at 80-90°C, keep it warm for 5 hours after the addition, and the reaction is over Afterwards, cool down to room temperature.

[0028] Add 900ml o-dichlorobenzene, 240.2g (1.5mol) of diethyl malonate, 59.3g-63.9g (0.75mol-0.75mol) of pyridine-piperidine into the flask, heat up to reflux, and keep warm for 3 hours; After the end, cool down to 10-20°C and filter; wash the filtrate three times with 500ml water, collect the organic layer, concentrate under reduced pressure to recover the solvent, the temperature of the reduced-pressure concentration is 70°C, and the gauge pressure is -0.096MPa; then carry out vacuum distillation , the temperature of vacuum distillation is 100 DEG C, the vacuum degree is more than 5mmHg, collects 184.7g of fractions of 80~85 DEG C / 5mmHg, is the product; content: 96.8% (HPLC).

Embodiment 3

[0030] Add 131.6g (1.8mol) of DMF into a 2000ml four-necked flask, raise the temperature to 80°C, slowly add 231.3g (1.5mol) of diethyl sulfate, control the temperature at 80-90°C, keep it warm for 3 hours after the addition, and the reaction is over Afterwards, cool down to room temperature.

[0031] Add 900 ml of dichloroethane, 240.2 g (1.5 mol) of diethyl malonate, 59.3 g to 63.9 g (0.75 mol to 0.75 mol) of pyridine-piperidine into the flask, heat up to reflux, and keep warm for 10 hours to react; After the end, cool down to room temperature and filter; first concentrate the filtrate under reduced pressure to recover the solvent, the temperature of reduced pressure concentration is 40°C, and the gauge pressure is -0.09MPa; then carry out reduced pressure distillation, the temperature of reduced pressure distillation is 98°C, the vacuum degree When the temperature is above 5mmHg, 176.1g of fractions at 80-85°C / 5mmHg are collected, which is the product; content: 98.3% (HPLC)...

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Abstract

The invention provides a preparation method of 3-N,N-dimethylaminoethyl acrylate. The preparation process comprises adding diethyl sulfate to dimethylformamide (DMF) at a molar ratio of 1:(1.1-1.3) for reacting to generate condensated salt; mixing with diethyl malonate, solvent and catalyst, heating until refluxing and reacting for 3-10 hours, and cooling to room temperature; filtering to remove the salt, washing the filtrate with water, mixing the organic layer, and depressing and distilling to remove solvent; and high vacuum distilling the residue, and collecting fraction of 80-85 DEC C / 5mmHg. The obtained 3-N,N-dimethylaminoethyl acrylate has yield and purity higher than that of optimal values in prior art.

Description

technical field [0001] The invention relates to a process for preparing 3-N,N-ethyl dimethylaminoacrylate, belonging to the technical field of fine chemicals. Background technique [0002] 3-N, N-dimethylamino-acrylic acid ethyl ester (Ethyl-3-(N, N-dimethylamine arcrylate or 3-Dimethylamino-acrylic acid ethyl ester), used as an intermediate of the quinolone drug moxifloxacin. 3-N , The synthetic method of ethyl N-dimethylaminoacrylate is as follows: ① take DMF (N, N-dimethylformamide) and ethoxyacetylene as raw materials to obtain by addition reaction, react at 20°C for 20 days, and the yield 25% (Recueil des Travaux Chimiques des Pays-BAS, 85(9-10), 929-51; 1966); ② Use tert-tert-butoxy-2-dimethylaminomethane and ethyl acetate as raw materials at 170°C Obtained by reacting for 20 hours with a yield of 88% (Chemische Berichte, 104(9), 2709-26; 1971); ③Use ethyl acrylate or diethyl malonate to make monopotassium salt with KOH, and then mix with DMF -Prepared by reaction of...

Claims

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Application Information

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IPC IPC(8): C07C229/30C07C227/14C07C227/00
Inventor 徐剑锋唐军
Owner SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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