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Electrochemical synthesis method of 2-substituted benzothiazole compound

The technology of a benzothiazole and a synthesis method, which is applied in the field of electrochemical organic synthesis, can solve the problems of increased operation difficulty, increased industrial cost, and high equipment requirements, and achieves the effects of low production cost, high product yield and low price.

Active Publication Date: 2020-06-26
SHAOGUAN COLLEGE
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the above method utilizes benzyl methyl ether as a raw material to obtain 2-substituted benzothiazole compounds with higher yields, in the synthesis process, it usually requires high temperature heating and excessive use of oxidants, resulting in increased industrial costs and operational Increased difficulty, higher requirements for equipment, and pollution to the environment. Such harsh synthesis conditions limit its wide application in industry

Method used

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  • Electrochemical synthesis method of 2-substituted benzothiazole compound
  • Electrochemical synthesis method of 2-substituted benzothiazole compound
  • Electrochemical synthesis method of 2-substituted benzothiazole compound

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preparation example Construction

[0037] Based on the above-mentioned reaction principle, the electrochemical synthesis method of the 2-substituted benzothiazole compounds of the present invention specifically includes the following steps:

[0038] (1) Add electrolyte, manganese salt catalyst, electrolytic solvent, benzyl ether compound and o-aminothiophenol in the electrolytic cell without diaphragm, insert anode and cathode, and carry out electrochemical reaction under stirring, electrification and constant current conditions;

[0039] Wherein, the molar ratio of the o-aminothiophenol to the benzyl ether compound is 1:1-1:1.5; the addition amount of the manganese salt catalyst is 10%-20% of the addition amount of the o-aminothiophenol; The molar concentration of the electrolyte in the electrolytic solvent is 0.1-0.2 mol / L; the electrochemical reaction conditions are: reaction time 2-4 hours, reaction temperature 45-60° C., and reaction current 15-30 mA.

[0040] And the electrolyte is any one or a combinatio...

Embodiment 1

[0044] In Example 1, 2-phenylbenzothiazole (3a) was synthesized by electrochemical synthesis using benzyl methyl ether (1a) and o-aminothiophenol (2a) as raw materials. The reaction principle is as follows:

[0045]

[0046] Wherein, in the present embodiment 1, the anode is a platinum electrode (Pt), the cathode is a platinum electrode ((Pt), and the electrolyte is lithium perchlorate (LiClO 4 ), the manganese salt catalyst is manganese sulfate monohydrate (MnSO 4 ·H 2 O), the electrolytic solvent is acetonitrile (CH 3 CN) and acetic acid (HOAc).

[0047] Specifically, a platinum electrode was used as an anode and a platinum electrode was used as a cathode, and 1 mmol LiClO was sequentially added to a round bottom flask 4 , 0.02mmol MnSO 4 ·H 2 O, 0.75mmol benzyl methyl ether, 0.5mmol o-aminothiophenol, 10mL CH 3 CN and 400μL HOAc were put into a magnetic stirrer, the cap was closed, the power was turned on, the current was adjusted to 20mA, and the electrolysis was ...

Embodiment 2

[0053] In Example 2, 2-(4-methylphenyl)benzothiazole (3b) was synthesized by electrochemical synthesis using benzyl tert-butyl ether (1b) and o-aminothiophenol (2a) as raw materials. The reaction principle is as follows:

[0054]

[0055] Wherein, in this embodiment 2, the anode is a platinum electrode (Pt), the cathode is graphite, and the electrolyte is ammonium perchlorate (NH 4 ClO 4 ), the manganese salt catalyst is manganese acetate tetrahydrate (Mn(OAc) 2 4H 2 O), the electrolytic solvent is acetonitrile (CH 3 CN) and trifluoroacetic acid (CF 3 COOH) mixture.

[0056] Specifically, a platinum electrode was used as the anode, graphite was used as the cathode, and 1 mmol NH 4 ClO 4 , 0.02mmol Mn(OAc) 2 4H 2 O, 0.75mmol benzyl tert-butyl ether, 0.5mmol o-aminothiophenol, 10mLCH 3 CN and 300 μL CF 3 COOH, put it into a magnetic stirrer, cover the bottle cap, turn on the power supply, adjust the current to 30mA, and electrolyze at 50°C for 2h. After the reacti...

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Abstract

The invention provides an electrochemical synthesis method of a 2-substituted benzothiazole compound. The method comprises the following steps of: (1) adding an electrolyte, a manganese salt catalyst,an electrolytic solvent, a benzyl ether compound and o-aminothiophenol into a diaphragm-free electrolytic tank, inserting an anode and a cathode, and carrying out electrochemical reaction under stirring, electrifying and constant-current conditions; and (2) after the reaction is finished, extracting the reacted solution, and performing separation and purification to obtain the 2-substituted benzothiazole compound. According to the invention, in a diaphragm-free single-chamber electrolytic tank, the benzyl ether compound and o-aminothiophenol are used as the raw materials to acquire the 2-substituted benzothiazole compound under the conditions of normal temperature, normal pressure and constant current; wherein the manganese salt is low in price, a peroxidant does not need to be additionally added in the synthesis process, the reaction conditions are mild and safe, the product yield is high, the production cost is low, meanwhile, the environmental pollution is small, the requirements of green chemistry are met, and a feasible scheme is provided for industrialization of the 2-substituted benzothiazole compound.

Description

technical field [0001] The invention relates to the technical field of electrochemical organic synthesis, in particular to an electrochemical synthesis method of 2-substituted benzothiazole compounds. Background technique [0002] Benzothiazole compounds have unique biological activity and are widely used in industry, medicine, agriculture and other fields. For example, in industry, benzothiazole compounds can be used as rubber vulcanization accelerators, dyeing machines for fibers, plastics, etc.; In medicine, benzothiazole compounds can be used as fungicides, etc.; in agriculture, benzothiazole compounds can be used as herbicides and insecticides. The modification of benzothiazole compounds is mainly to introduce different substituents on the benzene ring or to introduce different active groups at the 2-position. Since the 2-position substituent has the greatest influence on its activity, 2-substituted benzothiazoles The synthesis of such compounds is the most concerned p...

Claims

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Application Information

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IPC IPC(8): C25B3/00C25B11/04C07D277/66
CPCC07D277/66C25B3/00C25B11/04
Inventor 赖胤龙刘宏文严绍熙欧楚鸿张洁蓥谢张欣詹素丹涂松荣
Owner SHAOGUAN COLLEGE
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