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Synthesis method of 3-acetyl-2,5-dichlorothiophene

A technology of dichlorothiophene and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of high production cost, large amount of waste water, poor product purity, etc., and achieve the effect of reducing requirements and reducing investment

Inactive Publication Date: 2020-02-07
CHEM TECH ACAD OF SHANDONG PROVINCE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation method solves the problems of large amount of waste water, high production cost and poor product purity in the steps of the traditional 3-acetyl-2,5-dichlorothiophene synthesis process, and has the advantages of simple operation, environmental friendliness, high yield, The advantages of good product purity

Method used

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  • Synthesis method of 3-acetyl-2,5-dichlorothiophene

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Experimental program
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Effect test

Embodiment 1

[0033] Add 40g of 1-methyl-4-chlorobutenal to 200g of ethanol, stir and dissolve in a 500ml reaction bottle at a speed of 80 rpm, cool the reaction solution to -13°C, dissolve completely to form a solution, and add in batches Sodium ethylate 80g, feeding time 1.0h, after the feeding is finished, the temperature is raised to 0°C for 0.5h, after the reaction is finished, 80g of thioacetyl chloride solution is added dropwise to the reaction solution, and the temperature is raised to 60°C after the 1h dropwise addition process is completed, After reacting for 2 hours, distill ethanol off under reduced pressure, add 20 g of water to wash, separate the liquid, carry out rectification under reduced pressure on the organic phase, take 80-90 ° C fractions, and obtain 43.5 g of colorless transparent oily substance, the conversion rate is 75% , The gas phase content is 99.3%.

Embodiment 2

[0035] Add 100g of 1-methyl-4-chlorobutenal to 1000g of methanol, stir and dissolve in a 2500ml reaction bottle at a speed of 80 rpm, cool the reaction solution to -10°C, completely dissolve to form a solution, and add in batches Sodium methoxide 75g, the feeding time is 0.75h, after the feeding is finished, the temperature is raised to 2 degrees Celsius for 1 hour, after the reaction is finished, 60g of thioacetyl chloride solution is added dropwise to the reaction solution, and the temperature is raised to 80 degrees Celsius after 1.5 hours of dropping the process. After reacting for 1 hour, methanol was distilled off under reduced pressure, then 100 g of water was added to wash, the liquid was separated, and the organic phase was rectified under reduced pressure, and a fraction at 80-90 ° C was taken to obtain 108.9 g of a colorless transparent oil, with a conversion rate of 75.08% , The gas phase content is 99.4%.

Embodiment 3

[0037] Add 100g of 1-methyl-4-chlorobutenal to 600g of acetone, stir and dissolve in a 2000ml reaction bottle at a speed of 80 rpm, cool the reaction solution to -15°C, completely dissolve to form a solution, and add in batches Sodium bicarbonate 200g, the feeding time is 0.5h, after the feeding is finished, the temperature is raised to 10 degrees Celsius for 0.5 hours, after the reaction is finished, 70g of thioacetyl chloride solution is added dropwise to the reaction solution, and the temperature is raised to 75 degrees Celsius after 2 hours of the dropping process , reacted for 2 hours, after the acetone was distilled off under reduced pressure, 100 g of water was added to wash, and the liquid was separated, and the organic phase was subjected to vacuum distillation, and a fraction of 80-90 ° C was taken to obtain 117.6 g of a colorless transparent oil, with a conversion rate of 81.1 %, the gas phase content is 99.5%.

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Abstract

The invention discloses a synthesis method of 3-acetyl-2,5-dichlorothiophene and belongs to the field of organic synthesis. 1-methyl-4-chlorobutenal is added to a methanol solution, sodium methoxide is added after cooling, after thioacetylchloride is dropwise added, and a heating reaction is conducted to obtain the 3-acetyl-2,5-dichlorothiophene. The synthesis method is simple and convenient to operate, is green and environmentally friendly in production, the yield of the obtained product is higher, and the synthesis method is more suitable for mass production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 3-acetyl-2,5-dichlorothiophene. Background technique [0002] The synthetic method of 3-acetyl-2,5-dichlorothiophene, molecular formula: C 6 h 4 ClOS, molecular weight: 195.07. [0003] [0004] Brinzolamide is a carbonic anhydrase inhibitor developed by Alcon. It was approved by the U.S. Food and Drug Administration on April 1, 1998, approved by the European Drug Administration on March 9, 2000, and approved for marketing by the Japan Pharmaceuticals and Medical Devices Agency on October 8, 2002. Brinzolamide reduces the production of bicarbonate ions by inhibiting the carbonic anhydrase of the ciliary process, and subsequently reduces the delivery of sodium and water, thereby reducing the secretion of aqueous humor, and finally reducing the intraatrial pressure of the eye. This medicine is indicated to lower intraocular pressure in peopl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/28
CPCC07D333/28
Inventor 张智慧徐婷唐晓婵滕俊峰王灏
Owner CHEM TECH ACAD OF SHANDONG PROVINCE
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