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Chemical synthesis method of S-phenyl-4-tosylate

A technology of tosylate and chemical synthesis, applied in organic chemistry and other directions, can solve the problems of high risk factor, poor stability, high volatility, etc., and achieve the effects of environmental friendliness, low production cost, and three wastes.

Inactive Publication Date: 2012-07-04
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses thiophenol which is highly toxic, highly volatile, and has a foul smell as a raw material, which requires high equipment and has a high risk factor in the production process.
In addition, the p-toluenesulfonyl chloride used in this method is also a kind of sulfonyl chloride compound with high toxicity and poor stability.

Method used

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  • Chemical synthesis method of S-phenyl-4-tosylate
  • Chemical synthesis method of S-phenyl-4-tosylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The ratio of N-phenylmercaptosuccinimide and sodium p-toluenesulfinate is 1:1.0 according to the amount of feed material, N-phenylmercaptosuccinimide 20.7g (0.1mol); sodium p-toluenesulfinate 17.8g (0.1mol); The organic solvent is toluene 207g, and its total consumption is 10 times of the quality of N-phenylmercaptosuccinimide.

[0019] Sodium p-toluene sulfinate is dissolved in an organic solvent (the amount of the organic solvent is 6 times the mass of N-phenylmercaptosuccinimide). N-phenylmercaptosuccinimide is dissolved in an organic solvent (organic solvent consumption is 4 times of the quality of N-phenylmercaptosuccinimide), slowly added dropwise to the solution of sodium p-toluenesulfinate, the reaction temperature The temperature was 50°C, and the reaction was completed after 6 hours.

[0020] After the reaction was completed, the resulting reaction solution was added with saturated brine, extracted and separated to take the organic layer, and the organic laye...

Embodiment 2

[0023] The ratio of N-phenylmercaptosuccinimide and sodium p-toluenesulfinate is 1:1.5 according to the amount of feed material, N-phenylmercaptosuccinimide 20.7g (0.1mol); sodium p-toluenesulfinate 26.7g (0.15mol); The organic solvent is toluene 207g, and its total consumption is 10 times of the quality of N-phenylmercaptosuccinimide.

[0024] Other operations were the same as in Example 1 to obtain 23.2 g of S-phenyl-4-toluenesulfonate, with a yield of 88% and a purity of 98.8%.

Embodiment 3

[0026] The ratio of N-phenylmercaptosuccinimide and sodium p-toluenesulfinate is 1:1.5 according to the amount of feed material, N-phenylmercaptosuccinimide 20.7g (0.1mol); sodium p-toluenesulfinate 26.7g (0.15mol); the organic solvent is 207g of n-hexane, and its total consumption is 10 times of the quality of N-phenylmercaptosuccinimide.

[0027] The reaction temperature was 30°C and the reaction time was 7 hours. Other operations were the same as in Example 1 to obtain 21.9 g of S-phenyl-4-toluenesulfonate with a yield of 83% and a purity of 98.5%.

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Abstract

The invention discloses a chemical synthesis method of S-phenyl-4-tosylate shown as a formula (I). In the method, the S-phenyl-4-tosylate is obtained by taking sodium p-tolylsulfinate shown as a formula (II) and N-benzene mercaptosuccinimide as raw materials and fully reacting in an organic solvent at the temperature of 0-100 DEG C. The chemical synthesis method has the advantages of reasonable process condition, easiness and safety for operating, mild reaction conditions, high reaction yield, cheap and readily-available raw materials, environmentally-friendly substrate, low production cost, small quantity of three wastes, high implementation value and good social and economic benefits.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of S-phenyl-4-toluenesulfonate. (2) Background technology [0002] S-phenyl-4-toluenesulfonate is an important pharmaceutical and chemical intermediate, usually used in vulcanizing reagents, and has a wide range of applications in industry. [0003] Before the present invention was provided, the synthetic method of S-phenyl-4-tosylate in the prior art was to use p-toluenesulfonyl chloride and thiophenol as raw materials, and use dichloromethane as a solvent to synthesize S under the action of pyridine. -Phenyl-4-tosylate, eg Synthetic Communications, 1986, 16, 1709-1722. The method uses thiophenol which is highly toxic, highly volatile, and has a foul smell as a raw material, which requires high equipment and has a high risk factor in the production process. In addition, the p-toluenesulfonyl chloride used in this method is also a class of sulfonyl chloride compounds with high toxicity and poor...

Claims

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Application Information

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IPC IPC(8): C07C381/04
Inventor 陈久喜刘妙昌高文霞黄小波吴华悦
Owner WENZHOU UNIVERSITY
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