Method for utilizing inorganic metal sulfide to promote reaction of carbon disulfide and 2-halogen phenylamine to synthesize 2-mercaptobenzothiazole

A synthetic method and inorganic metal technology, which is applied in the fields of medicine, industry and agriculture, can solve problems such as environmental pollution and complex processing, and achieve the effects of simple post-processing, mild reaction conditions, 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

This method requires the use of strong base or expensive organic base DBU, whi

Method used

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  • Method for utilizing inorganic metal sulfide to promote reaction of carbon disulfide and 2-halogen phenylamine to synthesize 2-mercaptobenzothiazole
  • Method for utilizing inorganic metal sulfide to promote reaction of carbon disulfide and 2-halogen phenylamine to synthesize 2-mercaptobenzothiazole
  • Method for utilizing inorganic metal sulfide to promote reaction of carbon disulfide and 2-halogen phenylamine to synthesize 2-mercaptobenzothiazole

Examples

Experimental program
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Embodiment 1

[0015] Embodiment 1, using o-iodoaniline as raw material to synthesize 2-mercaptobenzothiazole (reaction temperature 130° C.)

[0016] In the reaction test tube, add 0.50mmol (0.1095g) of o-iodoaniline and 1.00mmol (0.2402g) of sodium sulfide nonahydrate, then add 2mL N, N-dimethylformamide and 1.50mmol ( 0.1142g) of carbon disulfide, stirred and reacted at 130°C for 12 hours. After the o-iodoaniline was completely reacted by TLC, the reaction solution was cooled to room temperature, added with 3 mL of 4N hydrochloric acid and stirred for 15 minutes, and then the reaction solution was extracted three times with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate for 2 hours, 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 chromatography (200-300 mesh silica gel), and gradient elution was carried out using ...

Embodiment 2

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

[0018] In the reaction test tube, add 0.50mmol (0.1095g) of o-iodoaniline and 1.00mmol (0.2402g) of sodium sulfide nonahydrate, then add 2mL N, N-dimethylformamide and 1.50mmol ( 0.1142g) of carbon disulfide, stirred and reacted at 90°C for 12 hours, after TLC detected that the o-iodoaniline had reacted completely, the reaction solution was cooled 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, 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 chromatography (200-300 mesh silica gel), and gradient elution was carried out using petroleum e...

Embodiment 3

[0019] Example 3, Synthesis of 2-mercaptobenzothiazole with o-iodoaniline as raw material (reaction temperature 110°C)

[0020] In the reaction test tube, add 0.50mmol (0.1095g) of o-iodoaniline and 1.00mmol (0.2402g) of sodium sulfide nonahydrate, then add 2mL N, N-dimethylformamide and 1.50mmol ( 0.1142g) of carbon disulfide, stirred and reacted at 110°C for 12 hours. After the o-iodoaniline was completely reacted by TLC, the reaction solution was cooled to room temperature, added with 3 mL of 4N hydrochloric acid and stirred for 15 minutes, and then the reaction solution was extracted three times with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate for 2 hours, 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 chromatography (200-300 mesh silica gel), and gradient elution was carried out using petrole...

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Abstract

The invention provides a method for synthesizing a 2-mercaptobenzothiazole derivate by utilizing 2-halogen phenylamine, carbon disulfide and inorganic metal sulfide as raw materials and relates to the field of medicines, industry and agriculture and the like. The synthesizing method comprises the steps of dissolving 2-halogen phenylamine and inorganic metal sulfide in an appropriate solvent, adding carbon disulfide to react for a certain time under the conditions of 90-130 DEG C, and performing purification treatment to obtain the product. The 2-mercaptobenzothiazole derivate can be synthesized rapidly and efficiently through the method, the raw materials used for the method are non-toxic, cheap and free of pollution, reaction conditions are moderate, aftertreatment is simple, and the yield is high.

Description

technical field [0001] The invention relates to the fields of medicine, industry and agriculture, in particular to a method for synthesizing 2-mercapto-substituted benzothiazole derivatives. Background technique [0002] 2-Mercaptobenzothiazole derivatives are important components of benzothiazole compounds and have wide application value in the fields of medicine, industry and agriculture. In medicine, 2-mercaptobenzothiazole is an important pharmaceutical intermediate. Biological experiments have shown that 2-mercaptobenzothiazole compounds have anticancer, antibacterial and other functions, and can also be used as proteinase inhibitors. In the rubber industry, 2-mercaptobenzothiazole (rubber vulcanization accelerator MBT) is a general-purpose vulcanization accelerator for rubber. It has the characteristics of fast vulcanization acceleration and no early vulcanization during mixing. It is an indispensable and efficient Rubber vulcanization accelerator is an essential raw ...

Claims

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Application Information

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IPC IPC(8): C07D277/72C07D277/70
CPCC07D277/70C07D277/72
Inventor 竺宁秦伟静洪海龙韩利民解瑞俊
Owner INNER MONGOLIA UNIV OF TECH
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