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Synthesis method of 2-arylbenzothiazole compound

A technology of benzothiazole and synthesis method, which is applied in the field of synthesis of 2-arylbenzothiazole compounds, can solve the problems of complex reaction system and high reaction temperature, and achieve the effects of easy-to-obtain raw materials, mild reaction conditions and simple steps

Active Publication Date: 2015-09-16
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The reaction system of this method is more complicated, as not only need copper salt catalyst, also need additives such as ligand, alkali, and reaction temperature is higher [referring to (a) W.R.Bowman, H.Heaney, P.H.G.Smith Tetrahedron, 1982,23,5093 .(b) E.A. Jaseer, D.J.C. Prasad, A. Dandapat, G. Sekar, Tetrahedron, 2010, 51, 5009.

Method used

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  • Synthesis method of 2-arylbenzothiazole compound
  • Synthesis method of 2-arylbenzothiazole compound
  • Synthesis method of 2-arylbenzothiazole compound

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0032] Embodiment 1: the synthesis of 2-phenylbenzothiazole

[0033]

[0034] Accurately measure the reaction substrate o-aminothiophenol (0.318mL, 3mmol), benzonitrile (0.306mL, 3mmol), and trifluoromethanesulfonic acid (3μL, 0.03mmol), and add them to a 25mL Schlenk bottle successively, Placed in an oil bath at 25°C for 14 hours. After stopping the reaction, extract with water and ethyl acetate as the extractant, and the extracted organic phase is washed with anhydrous Na 2 SO 4 After drying for 2 h and removing the solvent by rotary evaporation, the crude target product benzothiazole was obtained. This was followed by a recrystallization step: the crude benzothiazole was placed in a 50 mL flask. Put the flask into the heating mantle and heat it to 50°C, slowly add absolute ethanol dropwise until it is completely dissolved, then take the flask out of the heating mantle and let it cool down at room temperature for 4 hours, and filter it with filter paper after the white...

Embodiment 2

[0036] Embodiment 2: the synthesis of 2-(4-chloroaryl) benzothiazole

[0037]

[0038] Accurately measure the reaction substrate o-aminothiophenol (0.318mL, 3mmol), p-chlorobenzonitrile (0.412g, 3mmol), methanesulfonic acid (0.0028g, 0.03mmol), and add them to a 25mL Schlenk bottle in turn , placed in an oil bath at 40°C for 14 hours. After stopping the reaction, extract with water and ethyl acetate as the extractant, and the extracted organic phase is washed with anhydrous Na 2 SO 4 After drying for 2 h and removing the solvent by rotary evaporation, the crude target product 2-(4-chloroaryl)benzothiazole was obtained. This was followed by a recrystallization step: the crude 2-(4-chloroaryl)benzothiazole was placed in a 50 mL flask. Put the flask into the heating mantle and heat it to 50°C, slowly add absolute ethanol dropwise until it is completely dissolved, then take the flask out of the heating mantle and let it cool down at room temperature for 4 hours, and filter i...

Embodiment 3

[0040] Example 3: Synthesis of 2-(4-fluoroaryl)benzothiazole

[0041]

[0042] Accurately measure the reaction substrate o-aminothiophenol (0.318mL, 3mmol), p-fluorobenzonitrile (0.363g, 3mmol), D-camphor-10-sulfonic acid (0.139g, 0.6mmol), add to In a 25mL Schlenk bottle, put it in an oil bath at 50°C for 14h. After stopping the reaction, extract with water and ethyl acetate as the extractant, and use anhydrous Na2 SO 4 After drying for 2 h and removing the solvent by rotary evaporation, the crude target product 2-(4-fluoroaryl)benzothiazole was obtained. This was followed by a recrystallization step: the crude 2-(4-fluoroaryl)benzothiazole was placed in a 50 mL flask. Put the flask into a heating mantle and heat it to 50°C, slowly add absolute ethanol dropwise until it is completely dissolved, then take out the flask from the heating mantle and let it cool down at room temperature for 4 hours, and filter it with filter paper after the white crystals are completely preci...

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Abstract

The invention relates to the technical field of pharmaceutical chemical engineering intermediates and provides a synthesis method of a 2-arylbenzothiazole compound. The synthesis method comprises the following steps: (a) orderly adding an o-aminophenylthiophenol derivative, an aryl nitrile derivative and a protonic acid catalyst to a Schlenk bottle, putting the Schlenk bottle into oil bath for heating for reacting for 14 hours, and controlling the temperature within the range of 25-120 DEG C, wherein the molar ratio of the o-aminophenylthiophenol derivative to the aryl nitrile derivative is 1: 1, and the molar ratio of the o-aminophenylthiophenol derivative to the protonic acid catalyst is 1: (0.01-0.2); (b) after the reaction is ended, taking water and ethyl acetate as an extracting agent for extracting, and drying the organic phase after extracting by use of anhydrous Na2SO4, thereby obtaining a coarse target product benzothiazole; and (c) recrystallizing the coarse target product benzothiazole, and filtering by use of filter paper after white crystals are completely separated out, thereby obtaining the 2-arylbenzothiazole compound. The synthesis method is simple in steps, easily available in raw materials and mild in reaction conditions.

Description

technical field [0001] The invention relates to a method for synthesizing 2-arylbenzothiazole compounds, belonging to the technical field of pharmaceutical and chemical intermediates. Background technique [0002] 2-arylbenzothiazole is an important synthetic intermediate of drug molecules, and drugs containing its molecular skeleton structure often have good analgesic, antibacterial and antitumor activities; at the same time, 2-arylbenzothiazole is used in photoelectric materials Also very broad. Therefore, it is of great significance to develop new methods for the simple and economical synthesis of 2-arylbenzothiazoles. [0003] The main synthetic methods reported in the literature at present have the following three kinds: [0004] (1) Condensation reaction of o-aminothiophenolic compounds with carboxylic acids or aldehydes [0005] [0006] The reaction conditions of this method are very harsh, as need strong acid, high temperature reaction conditions, or need stro...

Claims

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Application Information

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IPC IPC(8): C07D277/66
CPCC07D277/66
Inventor 于晓强包明冯秀娟蒲子超
Owner DALIAN UNIV OF TECH
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