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Preparation method of 2-aryl benzothiazole compound

A technology for benzothiazole and compounds, which is applied in the field of preparation of 2-arylbenzothiazole compounds, can solve problems such as insufficient environmental protection of catalysts and limited range of substrates, and achieve cheap synthesis methods, low cost, and few by-products Effect

Pending Publication Date: 2020-04-28
EAST CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] However, the catalysts used in the above methods are not environmentally friendly, and the scope of substrates is limited, so it is necessary to develop a green preparation method with a wider range of application.

Method used

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  • Preparation method of 2-aryl benzothiazole compound
  • Preparation method of 2-aryl benzothiazole compound
  • Preparation method of 2-aryl benzothiazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A kind of preparation method of 2-aryl benzothiazole compound, its synthetic route is as follows:

[0037]

[0038] Specifically include the following steps:

[0039] (1) Take a 10mL Erlenmeyer flask or test tube, add 0.2mmol 2-aminothiophenol, 0.4mmol benzoylformic acid and 2mL deep eutectic solvent (the molar ratio of choline chloride to tartaric acid is 2:1);

[0040] (2) Put the Erlenmeyer flask or test tube in step (1) into a 60°C oil bath and stir magnetically for 30min to obtain the crude product;

[0041] (3) The crude product obtained in step (2) is separated by column chromatography, the eluent is a mixture of ethyl acetate and petroleum ether, the volume ratio is 1:6, and dried at 30°C for 3 hours to obtain 2-aryl Benzothiazole compounds.

[0042] Structural characterization of the obtained target product, the data are as follows:

[0043] White solid; m, p, 111.9-112.3°C; 1 H NMR (500MHz, CDCl 3 )δ8.12–8.08(m,3H),7.90(d,J=8.0Hz,1H),7.52–7.48(m,4H),7....

Embodiment 2

[0045]

[0046] A kind of preparation method of 2-arylbenzothiazole compound specifically comprises the following steps:

[0047] (1) Take a 10mL Erlenmeyer flask or test tube, add 0.2mmol 2-amino-4 chlorothiophenol, 0.4mmol benzoylformic acid and 2mL deep eutectic solvent (the molar ratio of choline chloride to tartaric acid is 2:1 );

[0048] (2) Put the Erlenmeyer flask or test tube in the step (1) into a 60° C. oil bath and stir magnetically for 30 minutes to obtain the crude product;

[0049] (3) The crude product obtained in step (2) is separated by column chromatography, the eluent is a mixture of ethyl acetate and petroleum ether, the volume ratio is 1:6, and dried at 30°C for 3 hours to obtain 2-aryl Benzothiazole compounds.

[0050] Structural characterization of the obtained target product, the data are as follows:

[0051] White solid; m.p.137-138℃; 1 H NMR (500MHz, CDCl 3 )δ8.09–8.05(m,3H),7.80(d,J=8.5Hz,1H),7.54–7.47(m,3H),7.36(d,J=8.5Hz,1H). 13 C NMR (1...

Embodiment 3

[0053]

[0054] A preparation method of 2-arylbenzothiazole compound, specifically comprising the following steps:

[0055] (1) Take a 10mL Erlenmeyer flask or test tube, add 0.2mmol 2-aminothiophenol, 0.4mmol p-toluoylformic acid and 2mL deep eutectic solvent (the molar ratio of choline chloride to tartaric acid is 2:1 );

[0056] (2) Put the Erlenmeyer flask or test tube in the step (1) into a 60°C oil bath and stir magnetically for 30min to obtain the crude product;;

[0057] (3) The crude product obtained in step (2) is separated by column chromatography, the eluent is a mixture of ethyl acetate and petroleum ether, the volume ratio is 1:6, and dried at 30°C for 3 hours to obtain 2-aryl Benzothiazole compounds.

[0058] Structural characterization of the obtained target product, the data are as follows:

[0059] Light yellow solid; m.p.81.5-81.9℃; 1 H NMR (500MHz, CDCl 3 )δ8.07(d, J=8.1Hz, 1H), 7.99(d, J=8.2Hz, 2H), 7.89(d, J=7.6Hz, 1H), 7.48(t, J=8.3Hz, 1H) ,7.37(t...

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Abstract

The invention discloses a preparation method of a 2-arylbenzothiazole compound, which comprises the following steps: adding a reaction substrate 2-aminothiophenol and ketonic acid(or aldehyde) into adeep eutectic solvent, magnetically stirring in an oil bath pot at 60-90 DEG C, and carrying out after-treatment after the reaction is finished to obtain the 2-arylbenzothiazole compound, wherein a deep eutectic solvent is a reaction solvent, and other catalysts are not needed. The method is simple to operate, mild in reaction condition, efficient in reaction, high in atom economy, few in byproducts and green and environment-friendly in reaction process, and has popularization and application values.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of a 2-arylbenzothiazole compound. Background technique [0002] 2-Arylbenzothiazole and its derivatives are condensed heterocyclic compounds containing nitrogen and sulfur, and have a wide range of uses. Due to its good biological activity, it is widely used as an important matrix and lead framework in drug innovations such as pesticides and medicines. In industry, it can also be used as rubber vulcanization accelerator, plastic dyeing agent, etc. Therefore, its synthesis and structural modification have attracted widespread attention. [0003] Currently, 2-arylbenzothiazole compounds have the following synthetic methods: [0004] Obtaining 2-arylbenzothiazole derivatives through direct arylation of benzothiazole compounds; [0005] Synthesis of 2-arylbenzothiazole derivatives by intramolecular cyclization of amides; [0006] Synthesis of 2-arylbenzothi...

Claims

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Application Information

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IPC IPC(8): C07D277/66
CPCC07D277/66Y02A50/30
Inventor 谢宗波陈国庆乐长高姜国芳孟佳朱海波张灿
Owner EAST CHINA UNIV OF TECH
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