Synthesis method of thiosulfonate compound

A technology of thiosulfonic acid ester and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of large environmental damage and cannot be applied to industrial production, etc., and achieves the effects of low reaction temperature and high conversion rate

Active Publication Date: 2018-06-22
GUANGDONG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of this, the present invention provides a synthetic method of thiosulfonate compounds, which is used to solve the problems in the prior art tha

Method used

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  • Synthesis method of thiosulfonate compound
  • Synthesis method of thiosulfonate compound
  • Synthesis method of thiosulfonate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] This embodiment is a specific example of synthesizing thio-p-tolylbenzenesulfonate.

[0068] Weigh 0.6mmol benzenesulfonyl hydrazide, 0.4mmol p-methylthiophenol, 0.2mmol sodium iodide and 2.5mL acetonitrile into a 15mL pressure-resistant reaction tube, then add 1.0mmol peroxy tert-butanol ( TBHP), adding a magnetic stirrer, stirring and reacting at 25°C for 6h, please refer to formula 1 for the chemical equation of this embodiment.

[0069] After the reaction was completed, acetonitrile was distilled off under reduced pressure at -0.090MPa and 40°C, and then 50 mL of dichloromethane was used for suction filtration under reduced pressure, and the obtained filtrate was distilled under reduced pressure at -0.085MPa and 35°C to remove methylene chloride, Purify by silica gel column chromatography with 200-300 mesh silica gel powder, the eluent is petroleum ether:ethyl acetate=50:1, and the yield of the obtained product is 100%.

[0070] figure 1 , figure 2 It is the NMR...

Embodiment 2

[0074] This embodiment is a specific example of synthesizing thio-p-tolylbenzenesulfonate.

[0075] Weigh 0.6mmol benzenesulfonyl hydrazide, 0.4mmol p-methylthiophenol, 0.2mmol sodium iodide and 2.5mL nitromethane into a 15mL pressure-resistant reaction tube, then add 1.0mmol tert-butyl peroxide dropwise into the reaction tube Alcohol (TBHP), adding a magnetic stirrer, stirring and reacting at 25° C. for 8 hours, please refer to formula 2 for the chemical equation of this embodiment.

[0076] After the reaction is over, carry out vacuum distillation at -0.095MPa and 40°C to remove nitromethane, then use 50mL of dichloromethane to carry out vacuum filtration, and the obtained filtrate is to carry out vacuum distillation at -0.085MPa and 35°C to remove dichloromethane , and then purified by silica gel column chromatography with 200-300 mesh silica gel powder, the eluent is petroleum ether:ethyl acetate=50:1, and the yield of the product obtained is 100%.

[0077] image 3 , ...

Embodiment 3

[0081] This embodiment is the specific embodiment of synthetic thio-p-tolylbenzenesulfonate

[0082] Weigh 0.6mmol of benzenesulfonyl hydrazide, 0.4mmol of p-methylthiophenol, 0.2mmol of sodium iodide and 2.5mL of 1,4dioxane (1,4dioxane) into a 15mL pressure-resistant reaction tube, and then pour into the reaction tube Add 1.0 mmol of tert-butanol peroxy (TBHP) dropwise, add a magnetic stirrer, and stir the reaction at 25° C. for 10 h. Please refer to Formula 3 for the chemical formula of this example.

[0083] After the reaction is over, carry out vacuum distillation at -0.095MPa and 45°C to remove 1,4-dioxane, then carry out vacuum filtration with 50mL of dichloromethane, and depressurize the obtained filtrate at -0.085MPa and 35°C The dichloromethane was distilled off, and purified by silica gel column chromatography with 200-300 mesh silica gel powder, the eluent was petroleum ether: ethyl acetate = 50:1, and the yield of the obtained product was 96%.

[0084] Figure 5 ...

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of a thiosulfonate compound. The invention provides the synthesis method of the thiosulfonate compound. The method comprises the following steps that methanesulfonohydrazide compounds, thiophenol compounds, oxidizing agents and catalysts are dissolved into a solvent for reaction; purification isperformed to obtain the thiosulfonate compound; oxidizing agents are any one kind or several kinds of materials from tertiary butanol peroxide and catalysts are sodium iodide, potassium iodide, ammonium iodide, iodine element and tetrabutylammonium iodide. Through experiment testing, the thiosulfonate compound prepared by the technical scheme provided by the invention has the advantages that no side reaction occurs; the yield can reach 84 to 100 percent; the conversion rate is high; meanwhile, the used catalysts and catalysts are environment-friendly compounds; the environment pollution cannot be caused; the reaction temperature is low; the method is suitable for industrial mass popularization. The defects that in the prior art, the damage to the environment in the asymmetric thiosulfonates synthesis process is great, and the application to industrial production cannot be realized are overcome.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing thiosulfonate compounds. Background technique [0002] Thiosulfonate and derivatives thereof, the general structural formula of which is It is a sulfonylation reagent that has been widely used in organic synthesis. In addition, this type of compound also has a broad spectrum of biological activities, such as antimicrobial agents and fungicides, so the synthesis of thiosulfonate esters Compounding is an important direction in the field of organic synthesis. The synthetic method of thiosulfonate compound is to obtain symmetrical thiosulfonate compound through direct oxidation of disulfide and mercaptan, but this synthetic method can only be used for synthesizing symmetrical thiosulfonate compound. [0003] In the prior art, there are the following three methods for asymmetric thiosulfonate compounds: first, sodium benzenesulfinate and disulfide are used...

Claims

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Application Information

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IPC IPC(8): C07C381/04C07D213/71C07D333/34
CPCC07C381/04C07D213/71C07D333/34
Inventor 陈迁黄昱霖吴佳微霍延平王肖峰余国典温春晓
Owner GUANGDONG UNIV OF TECH
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