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2-mercapto benzothiazole derivative synthetic method with copper-catalyzed carbon disulfide

A synthesis method and carbon disulfide technology, applied in organic chemistry and other directions, can solve the problems of many by-products, long reaction time and low yield, etc., and achieve the effects of simple operation, cheap raw materials and high yield.

Inactive Publication Date: 2014-10-15
INNER MONGOLIA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] There are many synthetic methods of 2-mercaptobenzothiazole, including o-nitrochlorobenzene method, aniline method, nitrobenzene method, nitrosobenzene method, benzothiazole method, nitrobenzene and aniline mixed method, N-methyl Aniline method, N, N-dimethylformamide method, dimethylamine method, halogenated aniline method and o-aminothiophenol method, etc., but most of these methods have long reaction time, low yield and many by-products

Method used

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  • 2-mercapto benzothiazole derivative synthetic method with copper-catalyzed carbon disulfide
  • 2-mercapto benzothiazole derivative synthetic method with copper-catalyzed carbon disulfide
  • 2-mercapto benzothiazole derivative synthetic method with copper-catalyzed carbon disulfide

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Embodiment 1

[0017] Embodiment 1, using o-iodoaniline as raw material to synthesize 2-mercaptobenzothiazole (reaction temperature 90°C)

[0018] Add 0.50mmol (0.1095g) of o-iodoaniline, 1.00mmol (0.2402g) of sodium sulfide nonahydrate and 0.05mmol (0.0095g) of cuprous iodide into the reaction test tube, and then add 2mL of solvent under an inert gas environment N,N-Dimethylformamide and 2.50mmol (0.1904g) of carbon disulfide were stirred at 90°C for 8 hours. After the reaction of o-iodoaniline was detected by TLC, the reaction solution was cooled to room temperature, and 3mL of 4N hydrochloric acid was added and stirred for 15min. , and then the reaction solution was extracted three times with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate for 2 hours, and then filtered to remove the desiccant, and finally the dichloromethane solvent was distilled off under reduced pressure to obtain a crude product. The crude product was separated by column chrom...

Embodiment 2

[0019] Embodiment 2, using o-iodoaniline as raw material to synthesize 2-mercaptobenzothiazole (reaction temperature 50°C)

[0020] Add 0.50mmol (0.1095g) of o-iodoaniline, 1.00mmol (0.2402g) of sodium sulfide nonahydrate and 0.05mmol (0.0095g) of cuprous iodide in the reaction test tube, and then add 2mL N , N-dimethylformamide and 2.50mmol (0.1904g) of carbon disulfide, stirred and reacted at 50°C for 8 hours, after the completion of the reaction of o-iodoaniline as detected by TLC, cooled the reaction solution to room temperature, added 3mL of 4N hydrochloric acid and stirred for 15min, Then the reaction solution was extracted three times with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate for 2 hours, and the desiccant was removed by filtration, and finally the dichloromethane solvent was distilled off under reduced pressure to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica ge...

Embodiment 3

[0021] Example 3, Synthesis of 2-mercaptobenzothiazole with o-iodoaniline as raw material (reaction temperature 70°C)

[0022] Add 0.50mmol (0.1095g) of o-iodoaniline, 0.25mmol (0.0600g) of sodium sulfide nonahydrate and 0.05mmol (0.0095g) of cuprous iodide in the reaction test tube, and then add 2mL N , N-dimethylformamide and 1.50 mmol (0.1142 g) of carbon disulfide were stirred and reacted at 70°C for 8 hours. After the reaction of o-iodoaniline was detected by TLC, the reaction solution was cooled to room temperature, and 3 mL of 4N hydrochloric acid was added and stirred for 15 min. Then the reaction solution was extracted three times with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate for 2 hours, and the desiccant was removed by filtration, and finally the dichloromethane solvent was distilled off under reduced pressure to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica gel)...

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Abstract

The invention relates to the technical field of agriculture, industry and pharmacy and provides a 2-mercapto benzothiazole derivative synthetic method. According to the 2-mercapto benzothiazole derivative synthetic method, 2-mercapto benzothiazole derivatives are synthesized by take 2-halogen phenylamine, carbon disulfide and inorganic metal sulfide as the raw materials and through catalysis of copper salt. The method comprises dissolving the 2-halogen phenylamine, the inorganic metal sulfide and copper salt catalyst inside an appropriate solvent, adding the carbon disulfide inside the mixture for recreation under 50-110 DEG C for a certain time and performing purification treatment to obtain the 2-mercapto benzothiazole derivatives. The 2-mercapto benzothiazole derivative synthetic method with the copper-catalyzed carbon disulfide is rapid and efficiency, by taking the nontoxic, cheap and easily-obtained copper salt as the catalyst, omits ligand for recreations, and has the advantages of being high in yield rate, mild in conditions, low in the amount of by-products and the like.

Description

technical field [0001] The invention relates to the technical fields of agriculture, industry and medicine, in particular to a method for synthesizing 2-mercapto-substituted benzothiazole derivatives. Background technique [0002] 2-Mercaptobenzothiazole derivatives are an important part of benzothiazole compounds and have wide application value in the fields of agriculture, industry and medicine. In agriculture, 2-mercaptobenzothiazole is an intermediate in the synthesis of the herbicide mefenacet. In industry, 2-mercaptobenzothiazole is widely used as a general-purpose rubber vulcanization accelerator to promote the vulcanization of natural rubber and synthetic rubber. In the field of medicine, 2-mercaptobenzothiazole compounds have anticancer, antibacterial and other functions, and can also be used as proteinase inhibitors. In addition, 2-mercaptobenzothiazole is also used in the preparation of fungicides, nitrogen fertilizer synergists, cutting oil and lubricant additi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/72C07D277/70
CPCC07D277/72C07D277/70
Inventor 竺宁秦伟静王留博洪海龙韩利民解瑞俊
Owner INNER MONGOLIA UNIV OF TECH
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