Preparation method of 2-phenylbenzothiazole derivative

A technology of derivatives, phenylbenzene, is applied in the field of preparation of 2-phenylbenzothiazole derivatives, and can solve the problems of large raw material pollution, long reaction steps, complicated post-processing and the like of 2-phenylbenzothiazole derivatives , to achieve the effect of simple and easy synthesis operation, low energy consumption and high atomic utilization rate.

Pending Publication Date: 2021-09-10
陕西维世诺新材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Based on the problems that the existing 2-phenylbenzothiazole derivative raw materials are polluted and expensive, the reaction steps are long, the reaction is complicated, the yield is low, and the post-treatment is complicated, the application provides a 2-phenylbenzothiazole derivative method of preparation

Method used

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  • Preparation method of 2-phenylbenzothiazole derivative
  • Preparation method of 2-phenylbenzothiazole derivative
  • Preparation method of 2-phenylbenzothiazole derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0043] Add 480ml polyphosphoric acid and 120ml phosphoric acid to a 1000ml reactor, heat up to 80°C, start stirring, then add (0.384mol, 48g) o-aminothiophenol and stir for half an hour, then add (0.384mol, 77g) p-bromobenzoic acid ; Heating up to 150°C, reacting for 1 hour, cooling down to 80°C, adding to 1200ml water to quench for 1 hour, filtering with suction funnel to obtain solid crude product, dissolving the solid crude product in ethyl acetate, passing through a silica gel column, and concentrating to obtain the fine product Product 2-(4-bromophenyl)benzothiazole, HPLC=99.2%, 102.5g yield 92%.

Embodiment 2

[0045] Add 480ml polyphosphoric acid and 120ml phosphoric acid to a 1000ml reactor, heat up to 80°C, start stirring, then add (0.384mol, 48g) o-aminothiophenol and stir for half an hour, then add (0.384mol, 77g) m-bromobenzoic acid ; Heating up to 160°C, reacting for 2 hours, cooling down to 90°C, adding to 1200ml water to quench for 1 hour, filtering with suction funnel to obtain solid crude product, dissolving the solid crude product in ethyl acetate, passing through a silica gel column, and concentrating to obtain the fine product Product 2-(3-bromophenyl)benzothiazole, HPLC=99.3%, 91.3g, yield 85%.

Embodiment 3

[0047]Add 480ml polyphosphoric acid and 120ml phosphoric acid to a 1000ml reactor, heat up to 80°C, start stirring, then add (0.384mol, 48g) o-aminothiophenol and stir for half an hour, then add (0.768mol, 105.2g) p-aminobenzene Formic acid; heat up to 170°C, react for 3 hours, cool down to 80°C, add to 1200ml water to quench for 1 hour, detect the raw material o-aminothiophenol through liquid phase to complete the reaction but there is a large excess of p-aminobenzoic acid, filter with suction The solid crude product was obtained by suction filtration through a funnel. The solid crude product was dissolved in ethyl acetate and passed through a silica gel column. After concentration, the crude product had a purity of 94.3%, and then recrystallized with ethanol to obtain the product 2-(4-aminophenyl)benzothiazole, HPLC=99.0 %, 45.1g yield 52%.

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a preparation method of a 2-phenylbenzothiazole derivative. An existing 2-phenylbenzothiazole derivative is high in raw material pollution, high in price, long in reaction step, complex in reaction, low in yield and complex in post-treatment. The invention provides the preparation method of the 2-phenylbenzothiazole derivative. Substituted aryl carboxylic acid and o-aminothiophenol are used as raw materials to react to obtain the 2-phenylbenzothiazole derivative. No waste solvent is generated, less waste water is generated, and the atom utilization rate is high, so that the method is more environment-friendly.

Description

technical field [0001] The application belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation method of 2-phenylbenzothiazole derivatives. Background technique [0002] The molecular formula of 2-phenylbenzothiazole is C13H9NS, which is insoluble in water. Due to its special structure, 2-phenylbenzothiazole derivatives have many applications. The introduction of different active groups in the 2 positions of its structure will have different applications and better performance in different fields. Due to the continuous research and development of organic electro-luminescent materials by scientists in recent years, the 2 positions introduced each Such substituents require higher and higher purity and yield, and with the continuous breakthrough and marketization of OLED organic light-emitting materials, there is a greater demand for its intermediate materials, so continuous innovation and continuous improvement of processes are...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66
CPCC07D277/66
Inventor 吕钟
Owner 陕西维世诺新材料有限公司
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