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Preparation method of sulfone compound

A technology of compounds and sulfones, which is applied in the field of preparation of sulfones, can solve problems such as limiting synthetic applications, achieve broad industrial application value, mild reaction conditions, and simple operation

Inactive Publication Date: 2017-12-08
XINYANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods all use special reaction substrates, which limit their further synthetic applications

Method used

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  • Preparation method of sulfone compound
  • Preparation method of sulfone compound
  • Preparation method of sulfone compound

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preparation example Construction

[0026] The preparation method of a kind of sulfone compound comprises the following steps:

[0027] a) dispersing the sulfonyl hydrazide with structure (I) in the cycloalkane solvent with structure (II);

[0028]

[0029] b) adding an iron salt catalyst and a peroxide oxidizing agent to the mixture obtained in step a), and reacting at a temperature of 90-130° C. for 6-12 hours to obtain a sulfone compound containing structure (III);

[0030]

[0031] When the R is an aryl group, the aryl group is phenyl or naphthyl;

[0032] When the R is a substituted aryl group, the substituted aryl group is p-chlorophenyl, p-tolyl, 2,4,6-trimethylphenyl, p-methoxyphenyl, m-methoxyphenyl , o-methoxyphenyl, p-trifluoromethylphenyl, p-tert-butylphenyl, p-fluorophenyl, p-iodophenyl, 3-nitro-4-chlorophenyl, 4-methyl-3 - fluorophenyl, p-acetamidophenyl or p-bromophenyl;

[0033] The said n is 1, 2, 3 or 4;

[0034] The iron salt is ferric chloride, ferrous sulfate, ferric oxide, ferric ...

Embodiment 1

[0042] In a clean and dry 10 ml Schlenk reaction tube, add 0.50 mmol p-toluenesulfonyl hydrazide, 1 ml cyclohexane, 0.025 mmol ferric chloride, and 1 mmol di-tert-butyl peroxide successively, and the reaction tube Seal and react at 120°C for 6 hours. After the reaction, the reaction mixture was directly spin-dried by a rotary evaporator to dry the cyclohexane in the reaction, and the remaining residue was separated by a silica gel column with petroleum ether as an eluent. , carbon spectrum and high-resolution mass spectrometry analysis confirmed that the target product was p-toluenecyclohexyl sulfone, and the yield was 80%.

[0043] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 1a As shown, the carbon NMR spectrum is shown as Figure 1b As shown, the high-resolution mass spectrum is shown as Figure 1c shown.

Embodiment 2

[0045] In a clean and dry 10 ml Schlenk reaction tube, add 0.50 mmol p-toluenesulfonyl hydrazide, 1 ml cyclohexane, 0.03 mmol iron sulfate, and 1 mmol di-tert-butyl peroxide in sequence, and seal the reaction tube , reacted at 130°C for 10 hours. After the reaction, the reaction mixture was directly spin-dried by a rotary evaporator to dry the cyclohexane in the reaction, and the remaining residue was separated by a silica gel column with petroleum ether as an eluent. , carbon spectrum and high-resolution mass spectrometry analysis confirmed that the target product was p-toluenecyclohexyl sulfone, and the yield was 68%.

[0046] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 1a As shown, the carbon NMR spectrum is shown as Figure 1b As shown, the high-resolution mass spectrum is shown as Figure 1c shown.

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Abstract

The invention discloses a preparation method of a sulfone compound. The method concretely comprises the following steps of (a) dispersing benzenesulfonyl hydrazide of a structure (I) into a cyclane solvent of a structure (II) (The structure (I) and the structure (II) are shown in the description); (b) adding catalysts of ferric salts and oxidants of peroxides into the mixture obtained in the step (a); then, performing reaction for 6 to 12h at the temperature being 90 to 130 DEG C to obtain the sulfone compound of a structure (III) (the structure (III) is shown in the description); R is aryl or substitutional aryl; the n is 1, 2, 3 or 4. The reaction conditions related by the synthesis method are mild; the cheap and easy-to-obtain ferric salts and peroxides are respectively used as catalysts and oxidants. The preparation method provided by the invention has the advantages that the cost is low; the operation is simple; mass production can be easily realized. Experiment results show that the yield of the obtained sulfone compound can reach a value as high as 80 percent.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of sulfone compounds. Background technique [0002] Today, organic sulfur chemistry has shown more and more extensive application prospects in many fields. In the polymer field, it can be used as a vulcanizing agent that provides a sulfur source to improve the tensile strength and toughness of various rubbers. In the field of medicine, it is an important organic intermediate of drugs for lowering blood pressure and drugs for preventing fatty liver. In the industrial field, it can be used as an anti-pressure and anti-wear additive for lubricating oil. Some sulfur compounds can also be used in feed additives, flavors and pesticides. Sulfone compounds containing sulfonyl groups are the most basic class of sulfur-containing organic compounds, so the construction of sulfone compounds has always been one of the focuses of organic chemistry research. [0003] D...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C317/14
CPCC07C313/04C07C315/00C07C317/14
Inventor 唐林杨禛饶伟浩马献涛周玉强
Owner XINYANG NORMAL UNIVERSITY
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