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Synthesis method of trimethoxystilbene

A technology of resveratrol trimethyl ether and a synthesis method, which is applied in the directions of ether preparation, sulfonic acid preparation, sulfonic acid amide preparation, etc., can solve the problems of difficult operation, difficult to scale up production, high price of trifluoromethanesulfonic anhydride, etc. Ease of operation and cost reduction

Inactive Publication Date: 2016-06-22
BAIYIN HAIRUIDA BIOCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material trifluoromethanesulfonic anhydride used in this method is expensive, and all of them are imported; a low-temperature reactor at minus 80 degrees is needed in the production, and the method has high cost, high requirements on equipment, difficult operation, and difficult to enlarge production

Method used

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  • Synthesis method of trimethoxystilbene

Examples

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Effect test

Embodiment 1

[0016] A synthetic method of resveratrol trimethyl ether, the reaction process is as follows figure 1 As shown, including the following steps:

[0017] 1) At room temperature, add 1 mol of trifluoromethanesulfonic acid to 1L of dichloromethane, stir and slowly add 0.5 mol of thionyl chloride dropwise, control the time for 55 minutes to complete the dropwise addition, stir and react at room temperature for 12 hours, the reaction system Concentrate to obtain crude trifluoromethanesulfonyl chloride, without purification, it can be directly used in the next reaction;

[0018] 2) Add 1 mol of aniline and 0.5 mol of triethylamine to 1L of dichloromethane, cool to 0°C, add 0.5 mol of the crude trifluoromethanesulfonyl chloride obtained in step 1) through a dropping funnel, and add dropwise After the completion, the temperature was raised to room temperature to react for 2 hours, and the reaction system was washed with water, dried, concentrated, and recrystallized with petroleum ether to ...

Embodiment 2

[0020] A synthetic method of resveratrol trimethyl ether, the reaction process is as follows figure 1 As shown, including the following steps:

[0021] 1) At room temperature, add 1 mol of trifluoromethanesulfonic acid to 1L of dichloromethane, stir and slowly add 1.5 mol of thionyl chloride dropwise, control the time for 65 minutes to complete the dropwise addition, stir and react at room temperature for 12 hours, the reaction system Concentrate to obtain crude trifluoromethanesulfonyl chloride, without purification, it can be directly used in the next reaction;

[0022] 2) Add 1 mol of aniline and 1.5 mol of triethylamine to 1L of dichloromethane, cool to 0°C, add 1.5 mol of the crude trifluoromethanesulfonyl chloride obtained in step 1) through a dropping funnel, and add dropwise After the completion, the temperature was raised to room temperature to react for 2 hours, and the reaction system was washed with water, dried, concentrated, and recrystallized with petroleum ether to ...

Embodiment 3

[0024] A synthetic method of resveratrol trimethyl ether, the reaction process is as follows figure 1 As shown, including the following steps:

[0025] 1) At room temperature, add 1 mol of trifluoromethanesulfonic acid to 1L of dichloromethane, stir and slowly add 1 mol of thionyl chloride dropwise, control the time for 60 minutes to complete the dropwise addition, stir at room temperature for 12 hours, and concentrate the reaction system The crude trifluoromethanesulfonyl chloride is obtained without purification and can be directly used in the next reaction;

[0026] 2) Add 1 mol of aniline and 1 mol of triethylamine to 1L of dichloromethane, cool to 0°C, and add 1 mol of the crude trifluoromethanesulfonyl chloride obtained in step 1) through a dropping funnel. After the addition is complete The reaction system was heated to room temperature for 2 hours, and the reaction system was washed with water, dried, concentrated, and recrystallized with petroleum ether to obtain resveratr...

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Abstract

The invention discloses a synthesis method of trimethoxystilbene. The method comprises the following steps of (1) at room temperature, adding trifluoromethanesulfonic acid into dichloromethane; stirring the mixture; slowly dripping sulfoxide chloride; after the dripping is completed, performing stirring reaction for 12 hours at room temperature; concentrating a reaction system to obtain a coarse product of trifluoromethanesulfonyl chloride; (2) adding aniline and triethylamine into dichloromethane; lowering the temperature to 0 DEG C; dripping the obtained coarse product of trifluoromethanesulfonyl chloride through a dropping funnel; after the dripping is completed, raising the temperature to room temperature for reaction for 2 hours; performing water washing, drying and concentration on the reaction system; then, performing recrystallization by petroleum ether to obtain trimethoxystilbene. The synthesis method has the beneficial effects that the raw materials of trifluoromethanesulfonic acid used by the synthesis method of trimethoxystilbene provided by the invention are common chemical raw materials; the price is low; the acquisition is easy; the cost is greatly reduced; special equipment such as low-temperature kettles is not needed in the production process; the operation is easy; the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a method for synthesizing resveratrol trimethyl ether. Background technique [0002] Resveratrol trimethyl ether is an important synthetic raw material for many antibacterial drugs, weight loss drugs, anticancer drugs and auxiliary agents. For example, preparation of H-PGDS inhibitors, Rho-kinase inhibitors, KSP inhibitors, CSF-1R inhibitors, renin inhibitors and the like with anticancer effects. In recent years, a series of new drugs with this type of compound as the key intermediate have been discovered, and the demand for this type of intermediate in the market is increasing day by day. However, through the investigation of the existing market, there are only a few large reagent companies in China that provide reagent-level gram-level small packages, and no unit can provide this product in batches. [0003] At present, it is known that the synthesis methods of res...

Claims

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Application Information

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IPC IPC(8): C07C41/01C07C43/23C07C303/38C07C311/48C07C303/02C07C309/80
CPCC07C41/01C07C303/02C07C303/38C07C43/23C07C311/48C07C309/80
Inventor 刘战朋
Owner BAIYIN HAIRUIDA BIOCHEM TECH CO LTD
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