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3-Amide-4-phenylcoumarin and preparation method thereof

Inactive Publication Date: 2019-10-01
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The invention provides a method for synthesizing novel coumarin derivatives 3-amide-4-phenylcoumarin under mild conditions, which solves the problem that the traditional production method of coumarin in the prior art takes highly toxic substances as The problem of high cost of raw materials and synthesis

Method used

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  • 3-Amide-4-phenylcoumarin and preparation method thereof
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  • 3-Amide-4-phenylcoumarin and preparation method thereof

Examples

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Effect test

Embodiment 1

[0034] A kind of synthetic method of 3-cyclohexyl amido-4-phenylcoumarin, comprises the following steps:

[0035] Under a nitrogen atmosphere, add 222mg of phenylpropiolate, 314mg of carbonyl (1-piperidinyl) acetic acid, 540mg of potassium persulfate, 17mg of silver nitrate, 2.5mL of water and 2.5mL of acetonitrile into a 25mL three-necked flask, and then The bottle was placed in an oil bath at 60°C, and the reaction was stirred at a magnetic stirring speed of 800r / min. During the reaction, the concentration of phenylpropiolate in the reaction liquid was monitored by thin-layer chromatography, and the reaction liquid was detected after 12 hours of reaction. The reaction of phenylpropiolate is complete, that is, the reaction is ended, and then the reaction solution is cooled to room temperature, filtered and concentrated to obtain 160 mg of 3-cyclohexylamide-4-phenylcoumarin in the form of white needles, with a yield of 60% .

[0036]

Embodiment 2

[0038] A kind of synthetic method of 3-cyclohexyl amido-4-phenylcoumarin, comprises the following steps:

[0039] Under a nitrogen atmosphere, add 222mg of phenylpropiolate, 314mg of carbonyl (1-piperidinyl) acetic acid, 540mg of potassium persulfate, 17mg of silver nitrate, 2.5mL of water and 2.5mL of acetonitrile into a 25mL three-necked flask, and then The bottle was placed in an oil bath at 100°C, and the reaction was stirred at a magnetic stirring speed of 800r / min. During the reaction, the concentration of phenylpropiolate in the reaction liquid was monitored by thin-layer chromatography, and the reaction liquid was detected after 12 hours of reaction. The reaction of the phenylpropiolate is complete, that is, the reaction is terminated, and then the reaction solution is cooled to room temperature, filtered, and concentrated to obtain 167 mg of white needle-like 3-amide 4-phenylcoumarin product with a yield of 50%.

Embodiment 3

[0041] A kind of synthetic method of 3-cyclohexyl amido-4-phenylcoumarin, comprises the following steps:

[0042] Under a nitrogen atmosphere, add 222mg of phenylpropiolate, 314mg of carbonyl (1-piperidinyl) acetic acid, 540mg of potassium persulfate, 17mg of silver nitrate, 2.5mL of water and 2.5mL of acetonitrile into a 25mL three-necked flask, and then The bottle was placed in an oil bath at 120°C, and the reaction was stirred at a magnetic stirring speed of 800r / min. During the reaction, the concentration of phenylpropiolate in the reaction liquid was monitored by thin-layer chromatography, and the reaction liquid was detected after 12 hours of reaction. The reaction of the phenylpropiolate is complete, that is, the reaction is terminated, and then the reaction solution is cooled to room temperature, filtered, and concentrated to obtain 163 mg of white needle-like 3-amide 4-phenylcoumarin product with a yield of 48%.

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a synthesis method of 3-amide-4-phenylcoumarin. Phenylpropiolic acid ester, oxamide, potassium persulfate, silver nitrate, natrium aceticum and a solvent are added into a reaction container in sequence for standby use; nitrogen is introduced into the reaction container, so that the inside of the reactioncontainer is in a nitrogen atmosphere; the reaction container is placed in an environment at 60-120 DEG C, a reaction is conducted at the stirring speed of 500-1,000 r / min, in the reaction process, the concentration of the phenylpropiolic acid ester in reaction liquid is monitored, and after it is monitored that the phenylpropiolic acid ester reacts completely, the reaction is finished; the reaction liquid is filtered and concentrated, and the 3-amide-4-phenylcoumarin is obtained. According to the synthesis method, under the mild condition, the 3-amide-4-phenylcoumarin is efficiently prepared, the cleanliness of the synthesis reaction is improved, the environmental pollution is reduced, and the adopted raw materials are single in type; the cost is reduced, and the economical efficiency ofthe technology is improved.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3-amide-4-phenylcoumarin. Background technique [0002] In the industrial synthesis of coumarin, the intermediate o-cresol phosphate is obtained through the action of o-cresol and phosphorus oxychloride, and chlorinated at 180 ° C to change the methyl group into -CHCl 2 , and then react with sodium acetate at 160-180°C for 5 hours for cyclization. [0003] With the development of environmental economy, the disadvantages of unsustainable development, high cost, and highly toxic raw materials exposed by traditional production methods urgently need to be replaced by more environmentally friendly and low-cost methods. Contents of the invention [0004] The invention provides a method for synthesizing novel coumarin derivatives 3-amide-4-phenylcoumarin under mild conditions, which solves the problem that the traditional production method ...

Claims

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Application Information

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IPC IPC(8): C07D311/12
CPCC07D311/12
Inventor 周明东杜海武孙京王贺
Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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