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Method for synthesizing multi-substituted benzothiazole derivative

A technology of benzothiazole and synthesis method, which is applied in the field of medicine, can solve problems such as difficult industrial production, complex synthesis steps, and difficult operation, and achieve the effects of short reaction time, simple operation, and mild reaction conditions

Inactive Publication Date: 2012-09-19
INNER MONGOLIA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the conditions for synthesizing benzothiazole derivatives with aromatic o-amino disulfides as raw materials are relatively harsh, requiring special reagents such as anhydrous and oxygen-free, high temperature, or using reducing agents. High, not easy for industrial production

Method used

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  • Method for synthesizing multi-substituted benzothiazole derivative
  • Method for synthesizing multi-substituted benzothiazole derivative
  • Method for synthesizing multi-substituted benzothiazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1, Synthesis of 6-(3,-dimethylphenoxy)-2-phenylbenzothiazol-5-amine (R'=H in the structural formula)

[0017]

[0018] 1, Synthesis of 6-(3,5 dimethylphenoxy)-2-phenylbenzothiazol-5-amine

[0019] In the 25ml round bottom flask, add 0.10mmol raw material 6,6'-dithiobis(4-(3,5-dimethylphenoxy)benzene-1,3-diamine), 4ml methanol solvent, under stirring After dissolving the raw material, 0.02 mmol of ferric chloride hexahydrate was added, and stirred to dissolve. Finally, 0.12 mmol of benzaldehyde was added, and the mixture was stirred and reacted at room temperature for 10 min. It was found by TLC that the reaction of the disulfide raw material was complete, and the crude product was obtained after removing the solvent by using a rotary evaporator under reduced pressure. The crude product was separated by column chromatography (200-300 mesh silica gel) with petroleum ether and ethyl acetate or dichloromethane and ethyl acetate as eluent, and a white solid with ...

Embodiment 2

[0024] Example 2, Synthesis of 6-(3,5-dimethylphenoxy)-2-(4-bromophenyl)benzothiazol-5-amine (R'=Br in the structural formula)

[0025]

[0026] 1, Synthesis of 6-(3,5-dimethylphenoxy)-2-(4-bromophenyl)benzothiazol-5-amine

[0027] In the 25ml round bottom flask, add 0.10mmol raw material 6,6'-dithiobis(4-(3,5-dimethylphenoxy)benzene-1,3-diamine), 4ml methanol solvent, under stirring After dissolving the raw material, 0.02 mmol of ferric chloride hexahydrate was added, and stirred to dissolve. Finally, 0.12 mmol of p-bromobenzaldehyde was added, and the mixture was stirred and reacted at room temperature for 10 min. TLC showed that the reaction of the disulfide raw material was complete, and the crude product was obtained after removing the solvent by using a rotary evaporator under reduced pressure. The crude product was separated by column chromatography (200-300 mesh silica gel) using petroleum ether and ethyl acetate or dichloromethane and ethyl acetate as eluents, and...

Embodiment 3

[0032] Embodiment 3, the synthesis of 6-(3,-dimethylphenoxy)-2-(4-methoxyphenyl)benzothiazol-5-amine (R'=OCH in the structural formula 3 )

[0033]

[0034] 1. 6-(3,5-dimethylphenoxy)-2-(4-methoxyphenyl)benzothiazol-5-amine

[0035] In the 25ml round bottom flask, add 0.10mmol raw material 6,6'-dithiobis(4-(3,5-dimethylphenoxy)benzene-1,3-diamine), 4ml methanol solvent, under stirring After dissolving the raw material, 0.02 mmol of ferric chloride hexahydrate was added, and stirred to dissolve. Finally, 0.12 mmol of p-methoxybenzaldehyde was added, and the mixture was stirred and reacted at room temperature for 10 min. TLC detection revealed that the reaction of the disulfide raw material was complete, and the crude product was obtained after removing the solvent by using a rotary evaporator under reduced pressure. The crude product was separated by column chromatography (200-300 mesh silica gel) using petroleum ether and ethyl acetate or dichloromethane and ethyl acetate...

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Abstract

The invention provides a method for synthesizing a multi-substituted benzothiazole derivative by using o-amino disulfide and aldehyde as raw materials, and relates to the technical field of medicine. The synthesizing method comprises the following steps of: dissolving the o-amino disulfide and the aldehyde into a proper solvent, reacting for 10 to 30 minutes at room temperature, and thus obtaining a product. The o-amino disulfide and the aldehyde which are simple, readily available and convenient to use are used as the raw materials and reacted under the catalyst of a cheap iron salt to quickly and efficiently synthesize the multi-substituted benzothiazole derivative. The method has the advantages that the raw materials are readily available, the operation is convenient, the reaction conditions are mild, the yield is high and the like.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a method for synthesizing multi-substituted benzothiazole derivatives. Background technique [0002] Multi-substituted benzothiazole derivatives are an extremely important class of heterocyclic compounds, which are widely used in the fields of pesticides, materials engineering, and medicine. In agriculture, it has anti-agricultural fungus, insecticide, acaricide, nematicide, anti-plant virus, weeding and other activities; in the field of material engineering, it can be used as a rubber vulcanization accelerator, plastic dyeing agent, liquid crystal display material, electrical Luminescent materials, photosensitive materials and fluorescent probe materials, etc. In medicine, it can be used as a fungicide, fungicide, anti-parasite, and can also be used for the treatment of diabetes, Alzheimer's disease and as a diagnostic reagent for tumors, anti-tuberculosis, anti-rheumatism, an...

Claims

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Application Information

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IPC IPC(8): C07D277/66
Inventor 竺宁韩利民张志伟洪海龙索全伶杜玉英
Owner INNER MONGOLIA UNIV OF TECH
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