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Method for preparing diethylamino ethanethiol

A technology of diethylaminoethanethiol and ethylaminoethanethiol, which is applied in the field of medicine, can solve the problems of consuming a large amount of organic solvents or water resources, the smell of sodium hydrosulfide is unpleasant, and it is not suitable for industrial applications, so as to reduce production costs , easy layering, and reduced production costs

Active Publication Date: 2008-08-27
保定加合精细化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method of sulfuric acid monoester and sodium hydrosulfide is to react diethylaminoethanol and sulfuric acid to generate sulfuric acid monoester, and then react sulfuric acid monoester and sodium hydrosulfide to generate diethylaminoethanethiol. The synthesis method is easy to carry out and easy to operate. Simple, cheap and easy to get raw materials, but in industrial production, sodium hydrosulfide smells bad, more than half of the side reactions in the mercaptolation process to generate diethylaminoethanol are inevitable, and diethylaminoethanethiol and diethylaminoethanol The boiling points are equal, and the products are difficult to separate
The diethylaminochloroethane and sodium hydrosulfide method is to obtain the diethylaminoethanol product by reacting diethylaminochloroethane and high-concentration sodium hydrosulfide to obtain the diethylaminoethanol product, but this synthetic method also has the similarity with the above-mentioned method Disadvantages, that is, the odor is unpleasant during industrial production, the reaction orientation is poor, and the reaction products are difficult to separate, etc.
The above-mentioned methods are not suitable for industrial applications, and consume a large amount of organic solvents or water resources

Method used

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  • Method for preparing diethylamino ethanethiol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 110 mol of thionyl chloride to 150 mol of benzene, and then add 100 mol of diethylaminoethanol dropwise to the above solution at a temperature of 35 to 40°C under external cooling conditions to form a reaction mixture. ℃ reflux reaction for 2h, then the reaction mixture is cooled to below 40 ℃, and 400mol water is added dropwise, then the reaction mixture is cooled to below 20 ℃, and the pH value of the reaction mixture is adjusted with a mass percent concentration of 50% sodium hydroxide solution 10. The reaction mixture was left to stand, and after the layers were separated, the upper oil layer was taken out, the lower water layer was extracted with benzene, and the extract was combined with the above oil layer, dried, filtered, and distilled to obtain diethylaminochloroethane, Its yield is about 90%, and its boiling point is about 134°C.

[0031] After adding 20 mol of thiourea and 0.002 mol of tetramethylammonium bromide into 200 mol of water, 22 mol of diethyla...

Embodiment 2

[0033] Take 150 mol of thionyl chloride and add it to 200 mol of chloroform or carbon tetrachloride. Under external cooling conditions, take 100 mol of diethylaminoethanol and add it dropwise to the above solution at a temperature of 30 to 35° C. to form a reaction mixture. The reaction mixture was refluxed at 60°C for 4 hours, then the reaction mixture was cooled to room temperature, filtered, and vacuum-rotated to obtain powdered diethylaminochloroethane hydrochloride with a yield of 96% and a melting point of 210-212°C about.

[0034] After adding 50mol of thiourea and 0.005mol of benzyltripropylammonium chloride into 500mol of water to dissolve, add 60mol of diethylaminochlorethane hydrochloride in batches at a temperature of 35-40°C, and let the reaction The mixture is incubated and reacted at a temperature of 70-75° C. for 3 hours, and then the potassium hydroxide solution with a mass percentage concentration of 40% in the reaction mixture is adjusted to pH = 13, and the...

Embodiment 3

[0036] Take 200mol of benzene and 110mol of thionyl chloride to form a mixed solution, drop 100mol of diethylaminoethanol into the above mixed solution at a temperature of 35-40°C under external cooling conditions to form a reaction mixture, and then put the reaction mixture Reflux at 75°C for 2 hours, then cool the reaction mixture to 40°C, and add 400 mol of water dropwise. After the reaction mixture is cooled below 20°C, add dropwise sodium hydroxide with a concentration of 45% by mass to adjust the pH of the reaction mixture. value of 10, the reaction mixture was left standing, and after the layers were separated, the oil layer was taken out, and the lower water layer was extracted with benzene, the extract was combined with the above oil layer, dried, filtered, and distilled to obtain diethylaminochloroethane, which The yield is 90%, and the boiling point is about 134°C.

[0037] Get the benzyltrimethylammonium chloride of 30mol thiourea 0.001mol and be dissolved in the 3...

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Abstract

A preparation method of diethylamino ethanethiol comprises chlorinating diethylamino alcohol via chlorinating agent to generate diethylamino chloroethane or relative hydrochloride, reacting the diethylamino chloroethane or relative hydrochloride with thiourea to generate S-substituted isothiourea salt, and processing alkaline hydrolysis on the S-substituted isothiourea salt via strong alkali to prepare diethylamino ethanethiol. The preparation method has simple process, low cost, reduced water consumption, reduced environment pollution, high reaction activity, better directionality, high product purity and high yield (at least 80%). The invention has wide application in medicine industry.

Description

technical field [0001] The invention specifically relates to a preparation method of diethylaminoethanethiol in the technical field of medicine. Background technique [0002] Tiamulin is one of the top ten veterinary antibiotics in the world, which can be used to prevent and treat diseases caused by mycoplasma infection, E. It has special effects on endemic pneumonia, endemic pneumonia and dysentery, and is widely used in aquaculture, especially in chicken and pig aquaculture. As a key intermediate in the production of tiamulin, diethylaminoethanethiol is in great demand in pharmaceutical companies. [0003] The inventor once designed and studied following several methods to the synthesis of diethylaminoethanethiol, i.e. sulfuric acid monoester and sodium hydrosulfide method, diethylaminochloroethane and sodium hydrosulfide method, sulfuric acid monoester and thiourea method and sulfide method. The method of sulfuric acid monoester and sodium hydrosulfide is to react diet...

Claims

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Application Information

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IPC IPC(8): C07C323/25C07C319/02
Inventor 王彦林叶进
Owner 保定加合精细化工有限公司
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