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Method for preparing substituted thiophenol and heterocyclic thiophenol by continuous flow reactor

A reactor, thiophenol technology, applied in the preparation of mercaptans, the formation/introduction of mercapto/thioether groups, and organic chemistry, etc., can solve the problems of limitation, long reaction steps, and less amount of three wastes, and reduce energy consumption. , to avoid flying temperature, the effect of reducing the amount of three wastes

Inactive Publication Date: 2018-12-28
ZHEJIANG YANGFAN NEW MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has a wide range of applications, and is applicable to raw materials containing aldehyde groups, ester groups, cyano groups, halogens, amides and other groups, especially for complex thiophenols or heterocyclic thiophenols compounds substituted by multifunctional groups synthesis, and the amount of three wastes is less, it can be used as a method of clean production, but the disadvantage of this route is that the reaction steps are longer, and a high temperature of 180-350 degrees is required for the rearrangement reaction. Conventional tank reactors are difficult to use for this rearrangement reaction. Reaction, so the industrial application of this route is limited

Method used

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  • Method for preparing substituted thiophenol and heterocyclic thiophenol by continuous flow reactor
  • Method for preparing substituted thiophenol and heterocyclic thiophenol by continuous flow reactor
  • Method for preparing substituted thiophenol and heterocyclic thiophenol by continuous flow reactor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046]

[0047] a. Add 6kg of ethylene dichloride and 1.63kg of tetramethylthiuram disulfide (TMTD) in the reaction flask, heat up to 60 degrees, add 700g of sulfuryl chloride dropwise, and keep the internal temperature between 60-65 degrees, After dripping and keeping warm for 2 hours, 200-300 g of dichloroethane was removed under reduced pressure, then cooled to room temperature, and the solid was removed by filtration to obtain the intermediate II solution, which was directly used in the next reaction.

[0048] b. Add 1221.2g 3-formylphenol in the reaction flask, add dropwise 1333.3g 30% liquid caustic soda, and control the temperature at the same time not to exceed 30°C. After dropping, slowly add the above-mentioned intermediate II solution to the system, and maintain the reaction temperature at 25°C. -35°C, keep the reaction for 2 hours after dropping, and adjust the pH to 6-7 with concentrated hydrochloric acid. The reaction solution was suction filtered, the filter ...

Embodiment 2

[0052]

[0053] a. With embodiment 1a.

[0054] b. Add 1221.2g 3-formylphenol, 1062.5g triethylamine, 3662.6g dichloroethane to the reaction flask, stir to dissolve, slowly add the above-mentioned intermediate II solution into the system, and maintain the reaction temperature at 25-35 ℃, after dripping, keep it warm for 2 hours, adjust the pH to 6-7 with concentrated hydrochloric acid, separate the liquid, desolventize the organic phase to obtain the crude product of intermediate II, recrystallize the crude product with ethanol, dry under reduced pressure to obtain intermediate III 2124.0g, yield 89.5%, liquid phase content 98.5%.

[0055] c. Add 2124.0g of intermediate III and 1000g of diphenyl ether into the reaction bottle, stir to dissolve, inject into the reaction pipeline by syringe pump (pipeline length 120m, Φ6*1mm), feed rate 150mL / min, oil temperature 255℃ ~275°C, hot water is cooled and flowed into another reaction bottle containing 1100g of 30% liquid caustic s...

Embodiment 3

[0058]

[0059] a. Add 6kg of ethylene dichloride and 1.63kg of tetramethylthiuram disulfide (TMTD) in the reaction flask, heat up to 60 degrees, add 700g of sulfuryl chloride dropwise, and keep the internal temperature between 60-65 degrees, After dripping and keeping warm for 2 hours, 200-300 g of dichloroethane was removed under reduced pressure, then cooled to room temperature, and the solid was removed by filtration to obtain the intermediate II solution, which was directly used in the next reaction.

[0060] b. Add 1451.6g 5-hydroxyisoquinoline in the reaction flask, add dropwise 1333.3g 30% liquid caustic soda, and control the temperature at the same time not to exceed 30°C. After dropping, slowly add the above-mentioned intermediate II solution to the system to maintain the reaction temperature 25-35°C, keep the reaction for 2 hours after dropping, adjust the pH to 6-7 with concentrated hydrochloric acid. The reaction solution was filtered with suction, the filter c...

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Abstract

The invention relates to a method for preparing substituted thiophenol and heterocyclic thiophenol by a continuous flow reactor. Phenol and phenol derivatives or heterocyclic phenol are taken as starting materials, and target compounds are prepared by four-step reactions of chlorination, esterification, rearrangement and hydrolysis, wherein the rearrangement reaction is conducted in the continuousflow reactor. According to the method, the reaction is guaranteed by a miniaturized heating device for high-temperature reaction and heat generated by the reaction, the conversion rate and the yieldhigher than those in the conventional reactor are obtained in the short residence time of tens of seconds, relevant side reactions are reduced, meanwhile, fluctuation of temperature and concentrationis avoided in the reaction process, temperature run-away and overheat are avoided, and the reaction process is safe and controllable.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a method for preparing substituted thiophenols and heterocyclic thiophenols by using a continuous flow reactor to carry out Newman-kwart rearrangement. Background technique [0002] Thiophenol and its derivatives are an important class of fine chemical products, which are widely used in medicine, pesticides, photocurable coatings, inks and other industries. Diltiazem The starting material is o-aminothiophenol; the drug raloxifene hydrochloride for the treatment of osteoporosis, the starting material is m-methoxythiophenol; the anti-hepatitis B drug amifovir disoproxil fumarate, the starting material is p- Methoxythiophenol; new antidepressant vortioxetine, the starting material is 2,4-dimethylthiophenol and so on. [0003] The existing methods for synthesizing thiophenol and its derivatives mainly include diazotization method, benzenesulfonyl chloride reduction metho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/06C07C323/62C07D217/02C07D231/18C07C323/09C07C323/19C07C321/26C07B45/06
CPCC07B45/06C07C319/02C07C333/04C07D217/02C07D231/18C07C323/62C07C323/09C07C323/19C07C321/26
Inventor 汤文杰林诗锐杨清沈小明李新林吴红辉樊彬
Owner ZHEJIANG YANGFAN NEW MATERIALS
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