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Preparation method of thiosulfonate compound

A technology of thiosulfonate and compound, which is applied in the field of preparation of photocatalytic thiosulfonate compound, which can solve the problems of a large amount of trifluoroacetic acid, high energy consumption, and corrosion of reaction equipment

Active Publication Date: 2021-05-18
CHINA ACAD OF SCI NORTHWEST HIGHLAND BIOLOGY INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, both methods require the use of a large amount of trifluoroacetic acid and heating conditions, which will severely corrode the reaction equipment and generate high energy consumption in actual production.

Method used

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  • Preparation method of thiosulfonate compound
  • Preparation method of thiosulfonate compound
  • Preparation method of thiosulfonate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] At room temperature, add photocatalyst rhodamine 6G (0.002mmol), aryl diazonium salt 1a (0.4mmol), sodium metabisulfite 2 (0.4mmol), p-cresol 3a (0.2mmol), acetonitrile 2mL, mix well. Then, under the irradiation of a 3W white LED lamp, the reaction was carried out at room temperature under nitrogen protection for 12 hours. After the reaction was detected by TLC, distilled water was added, and then the reaction solution was extracted with ethyl acetate, and the extract was concentrated in vacuum (0.08Mpa) to no solvent to obtain the crude product, and then the petroleum ether with a volume ratio of 5:1 Washing with a mixed eluent of ethyl acetate, followed by flash column chromatography on a silica gel column, the thiosulfonate 4aa of this example was obtained with a yield of 75%.

[0034] The resulting product spectrum data is:

[0035] 1 H NMR (500MHz, CDCl 3 ): δ7.58-7.56(m,3H),7.42(dd,2H,J=7.9,7.8Hz),7.23(d,2H,J=8.1Hz),7.13(d,2H,J=8.0Hz) ,2.37(s,3H)....

Embodiment 2

[0037]

[0038] At room temperature, add photocatalyst water-soluble eosin (0.002mmol), aryl diazonium salt 1a (0.4mmol), sodium metabisulfite 2 (0.4mmol), p-cresol 3a (0.2mmol), acetonitrile 2mL, mix well. Then, under the irradiation of a 3W white LED lamp, the reaction was carried out at room temperature under nitrogen protection for 12 hours. After the reaction was detected by TLC, distilled water was added, and then the reaction solution was extracted with ethyl acetate, and the extract was concentrated in vacuum (0.08Mpa) to no solvent to obtain the crude product, and then the petroleum ether with a volume ratio of 5:1 Washing with a mixed eluent of ethyl acetate, followed by flash column chromatography on a silica gel column, the thiosulfonate 4aa of this example was obtained with a yield of 56%.

[0039] The resulting product spectrum data is:

[0040] 1 H NMR (500MHz, CDCl 3 ): δ7.58-7.56(m,3H),7.42(dd,2H,J=7.9,7.8Hz),7.23(d,2H,J=8.1Hz),7.13(d,2H,J=8.0Hz) ,2.37...

Embodiment 3

[0042]

[0043] At room temperature, the photocatalyst Rose Bengal B (0.002mmol), aryl diazonium salt 1a (0.4mmol), sodium metabisulfite 2 (0.4mmol), p-cresol 3a (0.2mmol), Acetonitrile 2mL, mix well. Then, under the irradiation of a 3W white LED lamp, the reaction was carried out at room temperature under nitrogen protection for 12 hours. After the reaction was detected by TLC, distilled water was added, and then the reaction solution was extracted with ethyl acetate, and the extract was concentrated in vacuum (0.08Mpa) to no solvent to obtain the crude product, and then the petroleum ether with a volume ratio of 5:1 Washing with a mixed eluent of ethyl acetate, followed by flash column chromatography on a silica gel column, the thiosulfonate 4aa of this example was obtained with a yield of 70%.

[0044] The resulting product spectrum data is:

[0045] 1 H NMR (500MHz, CDCl 3 ): δ7.58-7.56(m,3H),7.42(dd,2H,J=7.9,7.8Hz),7.23(d,2H,J=8.1Hz),7.13(d,2H,J=8.0Hz) ,2.37(s,3H)...

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Abstract

The invention belongs to the field of organic synthetic chemistry, and particularly discloses a preparation method of a thiosulfonate compound. The specific preparation process comprises the following steps: taking aryl diazonium salt, sodium pyrosulfite and thiophenol / mercaptan as raw materials, taking organic dye as a photocatalyst, adding an organic solvent, and reacting for 12 hours at room temperature under the irradiation of an LED visible light lamp and nitrogen protection to generate thiosulfonate; and after the reaction is finished, adding distilled water into the reaction system, extracting the reaction liquid with ethyl acetate, concentrating the extraction liquid to obtain a crude product, and carrying out silica gel column chromatography separation on the crude product to obtain thiosulfonate. According to the method, simple and easily available sodium pyrosulfite is used as a sulfone source, cheap organic dye is used as a photocatalyst, clean light energy is used as a reaction energy source, a high-energy-consumption heating device and a metal catalyst or strong acid are not used, the reaction condition is mild, the operation is simple and convenient, and a green synthesis strategy is provided for thiosulfonate.

Description

technical field [0001] The invention belongs to the field of organic synthesis chemistry, and in particular relates to a preparation method of a photocatalyzed thiosulfonate compound. Background technique [0002] As a class of extremely valuable organic sulfides, thiosulfonate has important application value in the field of medicine. Compounds containing thiosulfonate structural units have a wide range of biological activities, such as insecticidal, antiseptic, antibacterial, antipyretic, anti-inflammatory, analgesic, and hypoglycemic. Therefore, the synthesis method of thiosulfonate compounds has attracted great attention of chemical researchers, and a variety of synthetic strategies have been developed by synthetic chemists. As shown in reaction formula 1, its synthetic method mainly comprises: strategy (1) obtains symmetrical thiosulfonate by oxidizing symmetrical disulfide; (3) The sulfidation reaction of sulfinate and -SR group-containing compounds to prepare symmetr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C381/04B01J31/02B01J31/04
CPCC07C381/04B01J31/0242B01J31/0244B01J31/04B01J31/0235B01J35/39
Inventor 吕玉芬魏伟岳会兰何林
Owner CHINA ACAD OF SCI NORTHWEST HIGHLAND BIOLOGY INST
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