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Preparation method of heterogeneously catalyzed 2-trifluoromethyl substituted benzimidazole compound

A technology of trifluoromethyl and benzimidazole, which is applied in the field of preparation of benzimidazole compounds, can solve the problems of unreported synthesis methods, etc., and achieve the effects of strong designability, simple post-treatment, and mild reaction conditions

Active Publication Date: 2021-09-24
HANGZHOU VOCATIONAL & TECHN COLLEGE
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, there is no report on the synthesis of trifluoromethyl-substituted benzimidazoles catalyzed by recyclable heterogeneous catalysts

Method used

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  • Preparation method of heterogeneously catalyzed 2-trifluoromethyl substituted benzimidazole compound
  • Preparation method of heterogeneously catalyzed 2-trifluoromethyl substituted benzimidazole compound
  • Preparation method of heterogeneously catalyzed 2-trifluoromethyl substituted benzimidazole compound

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Experimental program
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preparation example Construction

[0029] Catalyst preparation:

[0030] carbon nitride (g-C 3 N 4 ) was dispersed in DMF for three hours, and then ultrasonically treated carbon nitride, isonicotinic acid chloride hydrochloride and a few drops of triethylamine were mixed in DMF and reacted at 60°C for 6 hours. The reaction solution is centrifuged, washed and freeze-dried to obtain the complex of carbon nitride and isonicotinic acid chloride (g-C 3 N 4 -INCH). will g-C 3 N 4 -INCH and copper sulfate pentahydrate were mixed in the aqueous solution, triethylamine was added dropwise and reacted at 60°C for 3 hours. After the reaction is complete, the product is washed several times with DMF and ultrapure water, and freeze-dried to obtain a copper-doped carbon nitride catalyst (Cu / g-C 3 N 4 ).

[0031] Measurement of Cu / g-C using inductively coupled plasma optical emission spectrometer (ICP-OES) 3 N 4 The content of copper in the medium is 16%, and the transmission electron microscope (TEM) test Cu / g-C 3...

Embodiment 1～10

[0033] Add copper-doped carbon nitride, potassium carbonate, trifluoroethylimidoyl chloride (II), amine (III) and 2 mL of organic solvent into a 35 mL Schlenk tube according to the raw material ratio in Table 1, mix and stir evenly, and The reaction conditions of table 2 were reacted for 18-30 hours, filtered, mixed with silica gel, and purified by column chromatography to obtain the corresponding 2-trifluoromethyl-substituted benzimidazole compound (I). The reaction process is shown in the following formula:

[0034]

[0035] Table 1 The raw material addition of embodiment 1~10

[0036]

[0037] Table 2

[0038]

[0039] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Ph is phenyl, Me is methyl, i-Pr is isopropyl, n-Bu is n-butyl, n-Amyl is n-pentyl , Bn is benzyl, CF 3 It is trifluoromethyl, and DMF is N,N-dimethylformamide.

[0040] The structural confirmation data of the compounds prepared in Examples 1-5:

[0041] The nuclear ma...

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Abstract

The invention discloses a preparation method of a heterogeneously catalyzed 2-trifluoromethyl substituted benzimidazole compound, which comprises the following steps: adding copper-doped carbon nitride, potassium carbonate, trifluoroethylimido acyl chloride and amine into an organic solvent, reacting at 70-90 DEG C for 18-30 hours, and after the reaction is completed, filtering, washing and drying to obtain the heterogeneously catalyzed 2-trifluoromethyl substituted benzimidazole compound. And carrying out post-treatment to obtain the 2-trifluoromethyl substituted benzimidazole compound. The preparation method has the advantages of mild conditions, simple operation, cheap and easily available initial raw materials and high reaction efficiency; the copper heterogeneous catalyst can be recycled, different functional group substituted trifluoromethyl benzimidazole compounds can be synthesized through substrate design, the operation is convenient, and the applicability of the method is widened.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for preparing a heterogeneously catalyzed 2-trifluoromethyl-substituted benzimidazole compound. Background technique [0002] Benzimidazole compound is a very important nitrogen-containing heterocycle, which widely exists in the molecular skeleton of many natural products and functional materials (Bioorg.Med.Chem.Lett.2005,15,805-807). Benzimidazoles are also commonly used in fields such as dyes, polymers, fluorescent molecules, and corrosion science. The introduction of trifluoromethyl groups into the parent molecule can significantly improve its physicochemical properties, such as electronegativity, bioavailability, metabolic stability, and lipophilicity, etc. (J. Med. Chem. 2015, 58, 8315-8359). Therefore, the construction of trifluoromethyl-substituted benzimidazole compounds has important theoretical research significance and practical application value. [0003] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/10
CPCC07D235/10Y02P20/584
Inventor 王慧陈诺杨龙女陈玉发陈铮凯
Owner HANGZHOU VOCATIONAL & TECHN COLLEGE
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