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Method for synthesizing 4-halophenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydro-pyrimidin-2(1H)-one

A kind of technology of ethoxycarbonyl and halogenated phenyl, which is applied in the field of synthesis of 4-halogenated phenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one It can solve the problems of complex catalyst preparation process, long reaction time, limited application, etc., and achieve the effect of reducing the use of organic solvents and corrosive catalysts, simple and convenient processing, and mild reaction conditions.

Active Publication Date: 2018-06-08
DALIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned catalysts face problems such as long reaction time, complex catalyst preparation process, and easy deactivation of the catalyst, making it difficult to realize industrial production.
Sulfonic acid compounds can also be used as catalysts to catalyze the Biginelli reaction, such as p-toluenesulfonic acid [7] , sulfonic acid functionalized magnetite nanoparticles [8] etc., but the reaction catalyzed by sulfonic acid needs to be carried out in an organic solvent, sulfonic acid cannot be recovered, and the preparation process of loaded sulfonic acid is more complicated, which greatly limits the application of sulfonic acid catalyzed Biginelli reaction

Method used

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  • Method for synthesizing 4-halophenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydro-pyrimidin-2(1H)-one
  • Method for synthesizing 4-halophenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydro-pyrimidin-2(1H)-one
  • Method for synthesizing 4-halophenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydro-pyrimidin-2(1H)-one

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Experimental program
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Effect test

Embodiment 1

[0020] Reaction equation:

[0021]

[0022] Experimental method: Add 0.6mmol of catalyst DES, 2mmol of 4-fluorobenzaldehyde, 2mmol of ethyl acetoacetate and 3mmol of urea into a 25mL round-bottomed flask, stir the reaction for 40min at 70°C and stop the reaction. After the reaction, cool to room temperature, add ice-water mixture to fully separate the product, filter with suction, and wash with distilled water for 3 times to obtain the crude product. Recrystallization from ethanol-water solution can give 4-(4-fluorophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one with a yield of 91%.

Embodiment 2

[0024] Reaction equation:

[0025]

[0026] Experimental method: Add 0.6mmol of catalyst DES, 2mmol of 4-chlorobenzaldehyde, 2mmol of ethyl acetoacetate and 3mmol of urea into a 25mL round bottom flask, stir the reaction for 40min at 70°C and stop the reaction. After the reaction, cool to room temperature, add ice-water mixture to fully separate the product, filter with suction, and wash with distilled water for 3 times to obtain the crude product. Recrystallization with ethanol-water solution can give 4-(4-chlorophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one with a yield of 92%.

Embodiment 3

[0028] Reaction equation:

[0029]

[0030] Experimental method: Add 0.6mmol of catalyst DES, 2mmol of 4-bromobenzaldehyde, 2mmol of ethyl acetoacetate and 3mmol of urea into a 25mL round bottom flask, stir the reaction for 40min at 70°C and stop the reaction. After the reaction, cool to room temperature, add ice-water mixture to fully separate the product, filter with suction, and wash with distilled water for 3 times to obtain the crude product. Recrystallization with ethanol-water solution can give 4-(4-bromophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one with a yield of 88%.

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Abstract

The invention relates to a method for synthesizing 4-halophenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydro-pyrimidin-2(1H)-one. The method specifically comprises the following steps: with halogenated benzaldehyde, ethyl acetoacetate and urea as a substrate, and DES as a catalyst, stirring for reacting at a temperature of 60-75 DEG C under a solvent-free condition for 30-45 minutes, wherein a molar ratio of aromatic aldehyde to methyl acetoacetate to urea to DES is 1:1:1.5:0.3. According to the method disclosed by the invention, the cheap and readily available DES serves as the catalyst, any other solvent does not need to be added in the reaction process, ny other solvent and corrosive catalyst used can be effectively decreased, the reaction conditions are mild, and the method can be repeatedlyutilized and is simple in process, high in catalytic activity and high in yield; and moreover, the method is simple and convenient in reaction after-treatment, has environmental-friendly effect and isa cheap, safe and environmental-friendly synthetic method.

Description

technical field [0001] The invention relates to a method for catalytically preparing 4-halophenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one, more specifically, a A method for catalytically preparing 4-halophenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-ones by using a deep eutectic solvent through a Bininelli reaction. Background technique [0002] 3,4-dihydropyrimidin-2(1H)-one (DHPM) compounds are important pharmaceutical intermediates, which can be used as calcium channel agents, antiallergic agents, hypotensive agents, antagonists, etc., and also have antiviral, anti Biological activities such as tumor, antibacterial and anti-inflammatory [1] . [0003] In 1893, an Italian chemist first reported the synthesis of DHPM by using aromatic aldehyde, ethyl acetoacetate and urea under the catalysis of concentrated hydrochloric acid. This synthesis method is called Biginelli reaction. [2] . Although this method is simple and convenient, it has the ...

Claims

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Application Information

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IPC IPC(8): C07D239/22
CPCC07D239/22
Inventor 崔颖娜尹静梅贾颖萍李慎敏李长平
Owner DALIAN UNIV
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