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Environment-friendly chemical synthetic method for 3-pyridine sulfonyl chloride

A technology of pyridinesulfonyl chloride and green chemistry, applied in the direction of organic chemistry, can solve the problems of unfriendly environment, foul smell, high energy consumption, etc., and achieve the effects of reducing production costs, mild reaction conditions, and shortening reaction time

Active Publication Date: 2017-02-22
BEIJING THTD PHARMA TECH JOINT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Method 2 uses the expensive format reagent isopropylmagnesium chloride, which makes the cost of 3-pyridinesulfonyl chloride produced extremely high, and the reaction needs to occur under cryogenic conditions, which makes the energy consumption very high and cannot meet the requirements of energy saving and emission reduction
[0010] Method 3 uses 3-mercaptopyridine and chlorine as starting materials. 3-mercaptopyridine has a foul smell, and chlorine is also a highly toxic gas, so these two starting materials are extremely inconvenient to use, so the method environment also extremely unfriendly
[0011] Method 4 has used 3-aminopyridine as starting raw material, and this method avoids using phosphorus pentachloride and phosphorus oxychloride, makes this method belong to the category of green chemistry, but this method yield is low, makes the production of 3-pyridine The cost of sulfuryl chloride is extremely high

Method used

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  • Environment-friendly chemical synthetic method for 3-pyridine sulfonyl chloride
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  • Environment-friendly chemical synthetic method for 3-pyridine sulfonyl chloride

Examples

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Effect test

Embodiment 1

[0055] A green chemical synthesis method of 3-pyridinesulfonyl chloride, including the following steps:

[0056] Step A: Add 300kg of water to the reactor, and then pass in 200kg of sulfur dioxide after cooling to -10°C. During the process of passing in sulfur dioxide, the temperature is controlled not to be higher than 8°C. After the passage is completed, stir and add 211g of cuprous chloride to obtain sulfurous acid Aqueous solution, ready for use;

[0057] Step B: Add 63.76kg of 36% hydrochloric acid in another reactor, add 20kg of 3-aminopyridine, cool to -10°C, dropwise add sodium nitrite aqueous solution (containing 14.67kg sodium nitrite, 30kg water), The temperature of the dripping process is controlled not to be higher than 5℃, after the dripping is completed, the temperature is controlled to not higher than 5℃ for use;

[0058] Step C: Add the solution obtained in step B dropwise to the reactor of step A. The temperature of the dropping process is controlled at -5°C. After...

Embodiment 2

[0061] A green chemical synthesis method of 3-pyridinesulfonyl chloride, including the following steps:

[0062] Step A: Add 500kg of water to the reactor, add 126.43kg of thionyl chloride dropwise after cooling to 10°C, control the temperature at 0°C during the dropwise addition of thionyl chloride, add 422g cuprous chloride with stirring after the addition is complete , To obtain an aqueous solution of sulfurous acid, ready for use;

[0063] Step B: Add 106.27kg of hydrochloric acid with a mass fraction of 36% in another reactor, add 20kg of 3-aminopyridine, cool to 5°C, add dropwise sodium nitrite aqueous solution (containing 29.33kg sodium nitrite, 60kg water), dropwise During the addition, control the temperature at -5°C, after the addition is completed, control the temperature at -5°C, and set it aside;

[0064] Step C: Add the solution obtained in step B dropwise to the reactor of step A. The temperature of the dropping process is controlled at 5°C. After the dropping is comp...

Embodiment 3

[0067] A green chemical synthesis method of 3-pyridinesulfonyl chloride, including the following steps:

[0068] Step A: Add 350kg of water to the reactor, add 101.15kg of thionyl chloride dropwise after cooling to -5°C, control the temperature to 8°C during the dropwise addition of thionyl chloride, add 211g cuprous chloride after the addition is complete , To obtain an aqueous solution of sulfurous acid, ready for use;

[0069] Step B: Add 74.39kg of 36% hydrochloric acid in another reactor, add 20kg of 3-aminopyridine, cool to -10°C, dropwise add sodium nitrite aqueous solution (containing 14.67kg sodium nitrite, 30kg water), During the dropping process, the temperature is controlled at 5°C, after the dropping is completed, the temperature is controlled at 5°C, ready for use;

[0070] Step C: Add the solution obtained in step B dropwise to the reactor of step A. The temperature of the dropping process is controlled at -3°C. After the dropping is completed, the reaction is stirred...

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Abstract

The invention provides an environment-friendly chemical synthetic method for 3-pyridine sulfonyl chloride. The method comprises the steps of carrying out diazo-reaction, substitution reaction, extraction and distillation on 3-aminopyridine as a starting material, so as to obtain 3-pyridine sulfonyl chloride. By virtue of the method, acylation reagents such as pentachloride phosphorus oxychloride is not used, and reaction conditions are mild, so that the method for producing 3-pyridine sulfonyl chloride belongs to green chemistry, meanwhile, the reaction time is greatly shortened, the yield of the product is increased to be above 80%, and the production cost is greatly lowered.

Description

Technical field [0001] The invention relates to the technical field of green organic chemical synthesis, and specifically to a green chemical synthesis method of 3-pyridinesulfonyl chloride. Background technique [0002] Vonoprazan fumarate was approved for marketing in Japan on December 26, 2014. The drug belongs to a new class of inhibitors of potassium ion competitive acid blockers. Vonoprazan fumarate is fast-acting, powerful, and It has a long-lasting inhibitory effect on gastric acid secretion and also has an early termination effect on gastric acid secretion. The drug can be used clinically for erosive esophagitis, gastric ulcer, duodenal ulcer, and Helicobacter pylori eradication indications. [0003] 3-pyridinesulfonyl chloride is an important intermediate for the synthesis of vonoprazan fumarate. According to literature reports, there are roughly four methods for synthesizing 3-pyridinesulfonyl chloride: [0004] Method 1. The patents of the original manufacturer...

Claims

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Application Information

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IPC IPC(8): C07D213/71
CPCC07D213/71
Inventor 王红平
Owner BEIJING THTD PHARMA TECH JOINT CO LTD
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