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Method for realizing green synthesis of 2-substituted benzothiazole derivatives

A technology for benzothiazoles, green synthesis, applied in the direction of organic chemistry and the like, can solve the problems of unstable o-aminothiophenol, high cost of raw material preparation, long synthesis steps, etc., and achieves short steps, high yield and easy operation. Effect

Inactive Publication Date: 2016-08-24
INNER MONGOLIA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, o-aminothiophenol, N-aryl thioamide or thiourea, and o-haloaniline are mainly used as raw materials to synthesize benzothiazole derivatives; wherein o-haloaniline and N-aryl thioamide or thiourea The synthesis steps are relatively long and the cost of raw material preparation is relatively high
Therefore, o-aminothiophenol is usually used to react with aldehydes to synthesize benzothiazole derivatives, but o-aminothiophenol is unstable and is easily oxidized and dimerized to form disulfides, and most organic solvents are not environmentally friendly.

Method used

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  • Method for realizing green synthesis of 2-substituted benzothiazole derivatives
  • Method for realizing green synthesis of 2-substituted benzothiazole derivatives
  • Method for realizing green synthesis of 2-substituted benzothiazole derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Embodiment 1: take benzaldehyde as raw material to synthesize 2-phenylbenzothiazole

[0030] (1) Synthesis of 2-phenylbenzothiazole

[0031] a: Disulfide: Aldehyde: Na 2 S·9H 2 O=1:2:0.2

[0032] In the autoclave, add 0.40mmol of 2,2'-dithiodiphenylamine, 0.80mmol of benzaldehyde and 0.08mmol of Na 2 S·9H 2 O, put the magneton, then add 2 mL of water as the reaction solvent, heat it to 50 °C, and then fill with 2 MPa of carbon dioxide gas. Then continue to heat up to 80°C and stir for 24h. LC detection finds that the reaction of the disulfide raw materials is complete, cool to room temperature, and use a rotary evaporator to remove the solvent under reduced pressure to obtain a crude product. Using petroleum ether and ethyl acetate as eluents, the crude product was eluted with a gradient, and separated by column chromatography (200-300 mesh silica gel) to obtain 121.5 mg of 2-phenylbenzothiazole as a white powder with a purity of more than 99%. , the isolated yiel...

Embodiment 2

[0044] Example 2: Synthesis of 2-(4-chlorophenyl) benzothiazole with p-chlorobenzaldehyde as raw material

[0045] (1) Synthesis of 2-(4-chlorophenyl)benzothiazole

[0046] In the autoclave, add 0.40mmol of 2,2'-dithiodiphenylamine, 0.80mmol of p-chlorobenzaldehyde and 0.2mmol of Na 2 S·9H 2 O, put the magneton, then add 2 mL of water as the reaction solvent, heat it to 50 °C, and then fill with 2 MPa of carbon dioxide gas. Then continue to heat up to 80°C and stir for 24h. LC detection finds that the reaction of the disulfide raw materials is complete, cool to room temperature, and use a rotary evaporator to remove the solvent under reduced pressure to obtain a crude product. Using petroleum ether and ethyl acetate as eluents, the crude product was eluted with a gradient and separated by column chromatography (200-300 mesh silica gel) to obtain 2-(4-chlorophenyl) as a white powder with a purity greater than 99%. Benzothiazole 139.2 mg, isolated yield 71%, mp 112-113°C.

...

Embodiment 3

[0052] Embodiment 3: take p-bromobenzaldehyde as raw material to synthesize 2-(4-bromophenyl) benzothiazole

[0053] (1) Synthesis of 2-(4-bromophenyl)benzothiazole

[0054] In the autoclave, add 0.40mmol of 2,2'-dithiodiphenylamine, 0.80mmol of p-bromobenzaldehyde and 0.2mmol of Na 2 S·9H 2 O, put the magneton, then add 2 mL of water as the reaction solvent, heat it to 50 °C, and then fill with 2 MPa of carbon dioxide gas. Then continue to heat up to 80°C and stir for 24h. LC detection finds that the reaction of the disulfide raw materials is complete, cool to room temperature, and use a rotary evaporator to remove the solvent under reduced pressure to obtain a crude product. Using petroleum ether and ethyl acetate as eluents, the crude product was eluted with a gradient and separated by column chromatography (200-300 mesh silica gel) to obtain 2-(4-bromophenyl) as a white powder with a purity greater than 99%. Benzothiazole 187.2 mg, isolated yield 81%, mp 126-128°C.

[...

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Abstract

The invention provides a method for realizing green synthesis of 2-substituted benzothiazole derivatives. The method comprises the following steps of: contacting aldehyde, o-amido aroma disulphide and metal sulfide by taking water as a solvent in the present of CO2, so as to obtain 2-substituted benzothiazole derivatives. Compared with the prior art, the method has the characteristics that o-amido aroma disulphide and multiple types of aldehyde react under the effects of water and CO2, so that the 2-substituted benzothiazole derivatives are rapidly and efficiently synthetized, and the used raw materials are easily obtained and low in cost; the synthesis method has the advantages of simplicity and convenience in operation, short steps, high yield, easiness for product purification, environmental friendliness and the like.

Description

technical field [0001] The invention relates to the fields of medicine, pesticide and industrial technology, in particular to a method for synthesizing 2-substituted benzothiazole derivatives. Background technique [0002] 2-Substituted benzothiazoles and their derivatives are a very important class of heterocyclic compounds, which have broad application prospects in the fields of medicine, pesticide, and industry. In medicine, 2-substituted benzothiazole compounds are a very important class of pharmaceutical intermediates, with antibacterial, anticancer, antidiabetic and antituberculosis functions. In terms of pesticides, it can be used as insecticides and herbicides. In industrial production, it is a widely used chemical raw material, which can be used as a plastic dyeing agent and a raw material for making cosmetics. Since the first synthesis of 2-phenylbenzothiazole by Homfan in 1879, its synthesis method has become a research hotspot in organic chemistry. [0003] At...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C07D417/04
CPCC07D277/66C07D417/04
Inventor 竺宁刘波柳磊娄春情韩利民洪海龙闫丽岗
Owner INNER MONGOLIA UNIV OF TECH
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