Preparation method of diindolylmethanecompound

An indolylmethane and compound technology, which is applied in the field of preparation of bis-indolylmethane compounds, can solve the problems of poor atom economy, pollution, and difficulty in large-scale application, achieves efficient and clean production, reduces use costs, and saves The effect of resources

Active Publication Date: 2020-09-01
NINGXIA UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods are carried out in open containers, need to stir or grind; Ubiquitous catalyst is difficult to recycle, easily causes water pollution; Or catalyst preparation is complicated; Or in Lewis acid-surfactant combined (LASCs) catalyst system Preparation of a large amount of organic waste liquid containing toxic metals and surfactants due to demulsification and washing, especially the generation of toxic waste water containing a large amount of surfactant sodium lauryl sulfate, which is difficult to treat, etc.
In general, the yields of various catalytic reactions are not high, the subsequent purification waste is large, and a large amount of waste liquid is generated due to the use of a large amount of organic solvents to participate in the reaction. The atom economy of the whole process is very poor, resulting in high cost and serious pollution. , so it is difficult to apply on a large scale in industry

Method used

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  • Preparation method of diindolylmethanecompound
  • Preparation method of diindolylmethanecompound
  • Preparation method of diindolylmethanecompound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] P-Nitrobenzaldehyde (0.25mmol, 0.0418g) and indole (0.5mmol, 0.0585g) were respectively added into a pressure-resistant closed hydrothermal reaction kettle with a volume of 10 ml, and placed in a heater. Infrared measurement of the reactor temperature from room temperature to 160 ° C, and at this temperature to keep heating for 1 hour, stop heating; after the temperature of the reactor is reduced to room temperature (about 25 ° C), the reactor is opened, and by TLC thin layer chromatography ( The volume ratio is petroleum ether: ethyl acetate 3:1 (solvent is the developing agent) to track and monitor the reaction results. After initially confirming that the reaction is basically tending to completion, add dichloromethane (5mL×2) in batches and stir to disperse, then transfer Suction filtration in a suction filtration device, washing to dryness is the target product, and the product yield is 90%; the collected dichloroethane mother liquor is evaporated to recover the solv...

Embodiment 2

[0021] The feed ratio and the feed amount of the reaction substrate, the reaction vessel, and the basic operation process are the same as in Example 1, except that a small amount of water is added, and the temperature and time of the reaction are changed, and the yield results of the follow-up monitoring reaction are shown in Table 1. The results show that the addition of a small amount of water has an obvious thermodynamic catalytic effect at a temperature of 160-180°C.

[0022]

[0023] The influence result of table 1 temperature of reaction on reaction product yield

Embodiment 3

[0025] Add p-nitrobenzaldehyde (1 mol, 16.713 g), indole (2 mol, 23.430 g), and 8 ml of water respectively into a pressure-resistant closed reactor with a volume of 1 liter, and place it in a heater. Measure the temperature of the reactor by infrared rays from room temperature to 160°C, and keep heating at this temperature for 1 hour, then stop heating; after the temperature of the reactor drops to room temperature (about 25°C), open the reactor and take out the solid material in the reactor In an open container of 1 liter, and by TLC thin layer chromatography (volume ratio is sherwood oil: the solvent of ethyl acetate 3:1 is developing agent) follow-up monitoring reaction result, the content of preliminarily confirmed reaction product is close to 98%. Then, in the container containing the crude product, dichloromethane (300mL × 3) was added in batches, and after stirring and dispersing, it was transferred to a suction filtration device for suction filtration and washing to dry...

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Abstract

The invention discloses a preparation method of a diindolylmethane compound. The preparation method comprises the following steps: (1) respectively adding reaction substrate raw materials aromatic aldehydes and indoles and a trace amount of catalyst water into a reaction kettle; (2) heating to 110-180 DEG C in a closed state, and keeping for a certain time; (3) stopping heating, cooling the reaction kettle to room temperature to 80 DEG C, and adding an organic solvent to wash an obtained material into a collecting tank; and (4) carrying out solid-liquid separation, washing and recrystallization to obtain the target product diindolylmethane compound; and (5) collecting a solvent mother liquor and recovering the ttarget product, wherein the recovered solvent is reused. Compared with the prior art, the invention has the advantages of low cost and environmental protection.

Description

technical field [0001] The invention relates to the technical field of bis-indolylmethane compounds, in particular to a preparation method of bis-indolylmethane compounds. Background technique [0002] Bisindolylmethane (BIMs) derivatives are widely used in the fields of flavors and fragrances, dyes, medicine and agriculture, and are very important basic organic raw materials. The usual synthesis method is an alkylation reaction of indole compounds with aldehydes or ketones in a solvent under the catalysis of a catalyst. The catalysts used include acid catalysts such as protonic acid, Lewis acid, Lewis acid-surfactant, solid acid, etc.; the synthesis reaction is carried out in a solvent such as dichloroethane, or an aqueous phase system of water and surfactant. These methods are carried out in open containers, need to stir or grind; Ubiquitous catalyst is difficult to recycle, easily causes water pollution; Or catalyst preparation is complicated; Or in Lewis acid-surfactant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12C07D209/10C07D209/08C07D209/18C07D209/20
CPCC07D209/12C07D209/10C07D209/08C07D209/18C07D209/20
Inventor 刘万毅吴志强王刚刘睿波段斌相庆雨王旭军陈小燕
Owner NINGXIA UNIVERSITY
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