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A kind of preparation method of 1-arylethanesulfonic acid and derivative thereof

A technology of arylethanesulfonic acid and arylethanethiol, which is applied in the field of preparation of 1-arylethanesulfonic acid and derivatives thereof, can solve the problems of difficult separation, increased equipment cost, low reaction yield and the like, and achieves Mild reaction conditions, reduced environmental pressure, high yield and high purity

Active Publication Date: 2020-11-03
HENAN NEWLAND PHARMA
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0004] One is prepared by substitution reaction of 1-phenylbromoethane and sulfite, the reaction directly obtains a mixture of 1-phenylethanesulfonic acid and sulfite, and 1-phenylethanesulfonic acid is obtained after separation (Patent No.: CN103553977A); In this method, the mixture of 1-phenylethanesulfonic acid and sulfite is difficult to separate, it is difficult to obtain pure 1-phenylethanesulfonic acid, and the 1-phenylbromoethane The cost is high, and the highest yield stated in the patent is only 72.5%
[0005] The second is to adopt sodium disulfide to prepare diaryl disulfide, and then prepare 1-phenylethanesulfonic acid through oxidation (patent number: CN101792407A, CN102516133A); Increase the cost of equipment; or after the reaction, it is necessary to stand for stratification and extraction to separate the diaryl disulfide, which increases the process flow and time cost
[0006] There is also the preparation of 1-phenylethanesulfonic acid (patent number: 103613518A) by Grignard reagent method; but in the Grignard reaction, all raw materials required to be used are dry and anhydrous, and the requirements for operation are relatively high, and the production cost is relatively high
[0007] Also use thiourea and 1-phenylchloroethane to react to prepare 1-phenylethanethiol, and then prepare 1-phenylethanesulfonic acid (patent No.: CN102766076A) through oxidation reaction, this route is in the preparation of 1-phenylethane In the process of mercaptan, the hydrolysis and acidification step produces a large amount of waste water containing inorganic salts, which is difficult to handle, and the price of thiourea is relatively high, but the reaction yield is not high

Method used

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  • A kind of preparation method of 1-arylethanesulfonic acid and derivative thereof
  • A kind of preparation method of 1-arylethanesulfonic acid and derivative thereof
  • A kind of preparation method of 1-arylethanesulfonic acid and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] In a 1000ml four-necked bottle equipped with a stirrer, a condenser, and a thermometer, add 100ml of isopropanol and 20.3g of sodium hydrosulfide, start stirring, and start to add 34.0g of compound I dropwise, at a temperature of 30-35°C, dropwise 1-1.5 hours, after the dropwise addition, the temperature is raised to 50°C for heat preservation reaction for 10 hours, the heat preservation temperature is 50-55°C, controlled by GC, after the reaction is completed, the reaction is concentrated under reduced pressure, the organic solvent is recovered and the reaction is applied, and the obtained oil is Compound II . Then, 300.0 g of peracetic acid was added dropwise to the reaction bottle at room temperature for 4-5 hours. After the dropwise addition, the temperature was raised to 40-45°C, and the reaction was stirred for 12 hours. After drying, it was concentrated under reduced pressure and spin-dried, and desalted with methanol to obtain 42.4 g of compound III as an oil, w...

Embodiment 2

[0036] In a 1000ml four-neck flask equipped with a stirrer, a condenser, and a thermometer, add 100ml of ether, 20.3g of sodium hydrosulfide, start stirring, start to add 34.0g of compound I dropwise, dropwise at a temperature of 25-30°C, dropwise add 1- After 1.5 hours, continue to keep warm for 15 hours after the dropwise addition, controlled by GC, concentrate under reduced pressure after the reaction, recover the organic solvent and use it for the reaction, and the obtained oily substance is compound II. Then, 300.0 g of peracetic acid was added dropwise to the reaction bottle at room temperature for 4-5 hours. After the dropwise addition, the temperature was raised to 40-45°C, and the reaction was stirred for 12 hours. Concentrated under reduced pressure and spin-dried, and desalted with methanol, the obtained oil was 38.5 g of compound III, with a molar yield of 85.6% (calculated according to compound I), and a purity of 98.8%.

[0037]

Embodiment 3

[0039] In a 1000ml four-necked bottle equipped with a stirrer, a condenser, and a thermometer, add 100ml of isopropanol and 20.3g of sodium hydrosulfide, start stirring, and start to add 2.4g of compound I dropwise. The dropping temperature is 30-35°C. 1-1.5 hours, after the dropwise addition, the temperature is raised to 45°C for heat preservation reaction for 10 hours, the heat preservation temperature is 45-50°C, controlled by GC, after the reaction is completed, the reaction is concentrated under reduced pressure, the organic solvent is recovered and the reaction is applied, and the obtained oil is Compound II . Then, 300.0 g of peracetic acid was added dropwise to the reaction bottle at room temperature for 4-5 hours. After the dropwise addition, the temperature was raised to 40-45°C, and the reaction was stirred for 12 hours. Concentrated under reduced pressure and spin-dried, and desalted with methanol, the obtained oil was 45.8 g of compound III, with a molar yield of ...

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Abstract

The invention provides 1-aryl ethanesulfonic acid and a preparation method of its derivative. The preparation method comprises the following steps that (a) 1-aryl halogensated ethane represented in aformula (I) and sodium hydrosulfide react to generate 1-aryl ethanethiol; (b) 1-aryl ethanethiol performs oxidizing reaction to obtain 1-aryl ethanesulfonic acid. The 1-aryl halogensated ethane is used as a raw material, the 1-aryl ethanethiol is prepared through reaction of the 1-aryl halogensated ethane and the sodium hydrosulfide, and the 1-aryl ethanesulfonic acid is obtained through oxidization. The preparation method is simple in operation, reaction conditions are mild, the raw materials are cheap, the cost is low, the yield and purity are higher, and the method is a good process for preparing the 1-aryl ethanesulfonic acid. The solvent can be recycled, the environmental protection pressure can be reduced, the water content in the solvent does not affect the reaction degree, and no hydrolysis side reaction occurs. A chloro aryl compound can react with the sodium hydrosulfide, higher yield is obtained, the chloro aryl compound does not needs to be prepared, the cost can be remarkably reduced, and the yield is higher than the level of an existing process.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 1-arylethanesulfonic acid and derivatives thereof. Background technique [0002] Optically pure 1-arylethanesulfonic acid has a chiral center and is a strongly acidic sulfonic acid resolving agent. The artificially synthesized 1-arylethanesulfonic acid can be either D-isomer or L-isomer. Therefore, it is an excellent acidic resolving agent to replace camphorsulfonic acid and its derivatives in many aspects, and can be used for the resolution of compounds such as amino acids, basic drugs and basic intermediates. At present, the most researched 1-arylethanesulfonic acid is 1-phenylethanesulfonic acid. [0003] The synthetic route of relevant 1-phenylethanesulfonic acid mainly contains following several kinds at present: [0004] One is prepared by substitution reaction of 1-phenylbromoethane and sulfite, the reaction directly obtains a mixture o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/16C07C309/24
CPCC07C303/16C07C319/02C07C309/24C07C321/10
Inventor 谢建中郝小龙刘超袁兵
Owner HENAN NEWLAND PHARMA
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