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Preparation method of 3-formyl coumarin derivative

A technology of formyl coumarin and coumarin, which is applied in the field of preparation of 3-formyl coumarin derivatives, can solve the problems of dangerous use, transportation and storage, pollute the environment, corrode equipment and the like, and reduce resource consumption. , The reaction process is safe, the effect of small environmental pollution

Inactive Publication Date: 2017-07-18
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These halogenated reagents are toxic and corrosive and absorb moisture when exposed to air
Phosphorus trichloride and thionyl chloride will also produce a series of waste liquid and waste gas such as phosphoric acid and sulfur dioxide during use, which will corrode equipment and seriously pollute the environment.
However, phosgene is a highly toxic gas, which is very dangerous during use, transportation and storage.

Method used

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  • Preparation method of 3-formyl coumarin derivative
  • Preparation method of 3-formyl coumarin derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0022] The present embodiment provides the synthetic method of 3-formyl-7-diethylamino coumarin, and its main steps are as follows:

[0023] 1.08 g (4.97 mmol) of 7-diethylaminocoumarin was dissolved in 2 mL (26.03 mmol) of DMF, and 1.39 g (4.7 mmol) of BTC was slowly added dropwise under an ice-salt bath when the temperature was kept at -5 °C. A mixed solution of 5 mL of chloroform was added dropwise within 30 min. After all DMF was added dropwise, change to an oil bath, heat, control the temperature to 70°C, monitor the reaction progress by TLC, after 6 hours of reaction, pour directly into 80 mL of water, stir under an ice-salt bath for 10 min, extract with 10 mL of DCM, combine the organic phases under reduced pressure Distillation and ethanol recrystallization to obtain 0.94 g of 3-formyl-7-diethylaminocoumarin orange-red solid with a yield of 76.72%. Melting point 165.4~166.5 ℃.

Embodiment 2

[0025] The present embodiment provides the synthetic method of 3-formyl-7-methoxycoumarin, and its main steps are as follows:

[0026] 0.876 g (4.97 mmol) of 7-methoxycoumarin was dissolved in 2 mL (26.03 mmol) of DMF, and 1.39 g (4.7 mmol) of BTC and 1.39 g (4.7 mmol) of BTC and The mixed solution of 5 mL of chloroform was added dropwise within 30 min. After all DMF was added dropwise, change to an oil bath, heat, control the temperature to 70°C, monitor the reaction progress by TLC, after 6 hours of reaction, pour directly into 80 mL of water, stir under an ice-salt bath for 10 min, extract with 10 mL of DCM, combine the organic phases under reduced pressure Distillation, ethanol recrystallization to obtain 3-formyl-7-methoxycoumarin solid 0.72g, yield 70.12%. The melting point is 235.8~237.5℃.

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Abstract

The invention relates to a preparation method of a 3-formyl coumarin derivative. The preparation method comprises the following steps of: adopting coumarin or 7-substituted coumarin as a material, and reacting with bis(trichloromethyl) carbonate and N, N-dimethyl formamide to obtain a target compound. The preparation method has the advantages that solid phosgene is used for replacing a chlorinating agent containing phosphorus or sulfur, so that the problems of treatment of side products containing the phosphorus or the sulfur and discharge of waste water in the production process are solved. The preparation method has the characteristics that the materials are easily available, the cost is low, the operation is simple, the reaction condition is mild, the energy consumption is less, the reaction process is safe, the environmental pollution is less and clean production can be realized, and has industrial application prospect.

Description

technical field [0001] The invention relates to a preparation method of a 3-formyl coumarin derivative, in particular to the preparation of bistrichloromethyl carbonate, N,N-dimethylformamide and coumarin or 7-substituted coumarin Process for 3-formyl-7-substituted coumarins. Background technique [0002] Coumarin, also known as 1,2-benzopyrone or coumarin, exists in a large amount in natural plants and is an important natural product. Coumarin derivatives have significant biological and pharmacological activities, such as antithrombotic, anti-HIV and anti-cancer, and other pharmacological effects. At the same time, they also play an important role in plant physiology and can be used as plant hormones and growth regulators. It can also be used as enzyme inhibitor, antioxidant and so on. In addition, coumarin derivatives are also an important class of natural fragrances and are widely used in the fragrance industry. In addition, coumarin derivatives have unique photochemic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C07D311/12
CPCC07D311/16C07D311/12
Inventor 但飞君刘瑶鲁茜孙铭皓刘璐璐
Owner CHINA THREE GORGES UNIV
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