Method for synthesizing 3,3'-diindolylmethane

A technology of diindolylmethane and a synthesis method, which is applied in the field of synthesis technology of 3,3'-diindolylmethane, can solve the problems of poor catalytic performance, not easy to be environmentally friendly, complicated to operate, etc., and achieves reduction of energy consumption and material loss , saving reaction time and improving product yield

Active Publication Date: 2019-09-20
浙江财和生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Patent application number CN201410275713.3 discloses a method for preparing 3,3'-diindolylmethane by reacting indole and formaldehyde with methanol or ethanol as a reaction solvent under the condition of Michaelis acid as a catalyst. However, the The reaction uses organic acid as a catalyst. When water is used as the reaction medium, due to the poor water solubility of the catalyst and the poor catalytic performance, it can only react in methanol or ethanol, which is not easy to be environmentally friendly.
[0008] Patent application number CN201711204548.8 discloses a method of preparing 3,3'-diindolylmethane by reacting indole and formaldehyde with methanol or ethanol as the reaction solvent and sulfonic acid ion resin as the catalyst. Sulfonic acid ion resin has poor solubility in water, and the reaction can only have a good yield in methanol or ethanol
[0009] In the existing synthesis methods of 3,3'-diindolylmethane in the prior art, indole and formaldehyde are mainly used as the main raw materials to react through means such as catalyst catalysis or microwave, and some of these methods have relatively high requirements for catalysts. High, some operations are complicated and harsh; there are also indole-3-carbinol as the main raw material
In the method of using indole and aldehyde as the main raw material, the aqueous formaldehyde solution is used as the raw material, and the aqueous formaldehyde solution is relatively dangerous for storage and transportation.

Method used

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  • Method for synthesizing 3,3'-diindolylmethane
  • Method for synthesizing 3,3'-diindolylmethane

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Example 1: Add 280 grams of water, 120 grams of ethanol, 100.0 grams of indole, 15.4 grams of paraformaldehyde, and 7.4 grams of p-toluenesulfonic acid into a 1L three-necked flask, and react at 40-50° C. for 3 hours. TLC detects that the reaction is basically Stop stirring when complete, filter, wash with ethanol to obtain crude 3,3'-diindolylmethane, use toluene as solvent for crude product, recrystallize by heating, after cooling and precipitation is complete, filter its crystals, and dry in vacuum at low temperature to obtain a white solid 98.2 g, 93.4% yield, >99.0% purity. 1H NMR (500MHz, CDCl3): δ7.89(s, 2H), δ7.65(d, J=8.2Hz, 2H), δ7.38(d, J=8.2Hz, 2H), δ7.22(t , J=7.6Hz, 2H), δ7.12(t, J=7.6Hz, 2H), δ6.95(s, 2H), δ4.27(s, 2H).

Embodiment 2

[0020] Example 2: Add 280 grams of water, 120 grams of ethanol, 100.0 grams of indole, 15.4 grams of paraformaldehyde, and 14.7 grams of p-toluenesulfonic acid into a 1L three-necked flask, and react at 40-50°C for 3 hours. TLC detects that the reaction is basically Stop stirring when complete, filter, wash with ethanol to obtain crude 3,3'-diindolylmethane, use toluene as solvent for crude product, recrystallize by heating, after cooling and precipitation is complete, filter its crystals, and dry in vacuum at low temperature to obtain a white solid 99.0 g, yield 94.1%.

Embodiment 3

[0021] Example 3: Add 250 grams of water, 120 grams of ethanol, 100.0 grams of indole, 51.3 grams of 37% formaldehyde solution, and 7.4 grams of p-toluenesulfonic acid into a 1L three-necked flask, and react at 40-50° C. for 3 hours, and detect the reaction by TLC After it is almost complete, stop stirring, filter, and wash with ethanol to obtain the crude product of 3,3'-diindolylmethane. The crude product uses toluene as a solvent, and recrystallizes by heating. Solid 84.1 g, yield 80.0%.

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Abstract

The invention provides a method for synthesizing 3,3'-diindolylmethane. The method includes taking benzazole and paraformaldehyde as reaction raw materials, taking p-toluenesulfonic acid as a catalyst, reacting the three in a water and ethanol mixed solvent to obtain a crude product of the 3,3'-diindolylmethane, and recrystallizing the crude product to obtain a finished product. The method has the advantages of simplicity, safety process, simple operation, high yield and convenience for industrial production.

Description

technical field [0001] The invention relates to the fields of medicine and chemical industry, in particular to the field of a synthesis process method of 3,3'-diindolylmethane. Background technique [0002] 3,3'-Diindolylmethane (3,3'-Diindolylmethane) is white to off-white crystalline powder, soluble in methanol, ethyl acetate, dichloromethane and other organic solvents. 3,3'-Diindolylmethane widely exists in natural plants of the Brassicaceae family. It has important biological and pharmacological activities and is widely used in the fields of medicine and health products. [0003] [0004] In the existing synthesis methods of 3,3'-diindolylmethane, indole and aldehydes are mainly used, and indole-3-carbinol, indole and N-methacrylamide are used as main raw materials. Some of these synthetic methods have higher requirements on catalysts, and some of them are complex and harsh in operation. Therefore, there is an urgent need in this field for an industrially effective ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 薛凌霄王明江世坤张文
Owner 浙江财和生物科技有限公司
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