Preparation method of 2-methyl-3-(2-amino) ethylidenethio-vinylpropionate

A technology of ethylidene thiovinylpropionate and aminoethanethiol, which is applied in the field of organic chemical synthesis reagents, can solve problems such as residual side reactions and harmful effects, and achieve improved reaction selectivity, wide application range, and practical industrial application value Effect

Inactive Publication Date: 2016-06-08
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such addition reactions usually use strong bases and strong acids to activate nucleophil

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: in the ground mouth Erlenmeyer flask of 150ml, first add 50ml ionic liquid hydroxide [1-butyl-3-methylimidazole], add 0.1mol β-amino ethanethiol in the Erlenmeyer flask, fully After mixing, add 0.1mol vinyl methacrylate, shake at a speed of 200 rev. / min in a constant temperature shaking incubator at 25°C; TLC monitors the reaction progress, and it shows that the reaction is complete after 15 minutes. After the end, add 60ml of Ethyl acetate was extracted 5 times, and after the extracts were combined, the water pump decompressed distillation to recover ethyl acetate, weighed, and the yield of the product was 94.0%; using silica gel as a filler, the product was purified by column chromatography, and the product was purified by nuclear magnetic resonance spectroscopy. For characterization, the characterization of H NMR and C NMR can be seen in the determination of the structure, and the results are as follows:

[0034] 1 HNMR (CDCl 3 ,500MHz,δ,ppm):7.29(dd,...

Embodiment 2

[0036] Embodiment 2: In the ground mouth Erlenmeyer flask of 150ml, first add 50ml ionic liquid hydroxide [1-butyl-3-methylimidazole], add 0.1mol β-amino ethanethiol in the Erlenmeyer flask, fully After mixing, add 0.11mol vinyl methacrylate, shake at a speed of 200 rev. / min in a constant temperature shaking incubator at 25°C; TLC monitors the reaction process, and it shows that the reaction is complete after 15 minutes. After the end, add 60ml of Ethyl acetate was extracted 5 times, and after the extracts were combined, the water pump decompressed distillation to recover ethyl acetate, weighed, and the yield of the obtained product was 94.5%.

Embodiment 3

[0037] Embodiment 3: in the ground mouth conical flask of 150ml, first add 50ml ionic liquid hydroxide [1-butyl-3-methylimidazole], add 0.1mol β-amino ethanethiol in the conical flask, fully After mixing, add 0.12mol vinyl methacrylate, shake at a speed of 200 rev. / min in a 25°C constant temperature shaking incubator; TLC monitors the reaction process, and it shows that the reaction is complete after 15 minutes. After the end, add 60ml of Ethyl acetate was extracted 5 times, and after the extracts were combined, the water pump decompressed distillation to recover ethyl acetate, weighed, and the yield of the obtained product was 95.1%. .

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PUM

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Abstract

The invention discloses a preparation method of 2-methyl-3-(2-amino)ethylidenethio-vinylpropionate. The preparation method comprises: in a reactor adding a basic ionic liquid and then 2-aminoethanethiol reagent, and mixing well; after mixing, adding 2-vinyl methacrylate, and reacting by oscillating at a speed of 200 rev./min in a constant-temperature oscillating box; after reaction is over, adding an exacting agent to a mixed liquid for exacting, and combining extract liquids and distilling under reduced pressure to obtain a product, with recycled extracting agent for cyclic use. Polyfunctional 2-methyl-3(2-amino)ethylidenethio-vinylpropionate is prepared by accelerating reaction of 2-aminoethanethiol and 2-vinyl methacrylate by using a basic ionic liquid, the selective and sulfydryl actions of the basic ionic liquid enable their conversion into sulfur negative ions of higher nucleophilicity, and priority is given to high-speed, high-efficiency and high-selectivity Michael addition reaction with vinyl methacrylate when compared to amino, while Markovnikov's and anti-Markovnikov's additions of vinyl do not occur.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis reagents, in particular to promoting the reaction of 2-aminoethanethiol reagent and 2-methacrylic acid vinyl ester with alkaline ionic liquid, and preparing 2-methyl-3-(2 -Amino)ethylidenethiopropionate method. technical background [0002] Chemistry constantly creates new substances to meet the needs of people's material and cultural life. Green chemistry aims to ensure the sustainable development of human society. Modern synthetic chemistry realizes low-cost, safe, and atom-economical synthesis through the chemical and regioselective control of unimolecular elementary reactions, meeting the requirements of green and sustainable chemistry. [0003] Avoiding the formation of carbon-sulfur bonds involving transition metals can prevent the impact of harmful metal substances on people's living environment and human health, and open up new development prospects for organic chemistr...

Claims

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Application Information

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IPC IPC(8): C07C319/18C07C319/28C07C323/52
CPCC07C319/18C07C319/28C07C323/52
Inventor 娄凤文杜艳秋朱凤霞孙小军安礼涛
Owner HUAIYIN TEACHERS COLLEGE
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