Synthetic method of benzimidazole compounds

A synthesis method and technology of benzimidazole, which are applied in the field of synthesis of benzimidazole compounds, can solve the problems of inability to recycle and reuse catalysts, complicated product post-processing, difficult catalyst preparation, etc., and achieve good practical value and social and economic efficiency, The effect of saving cost and labor input, and easy operation of post-processing

Active Publication Date: 2018-12-28
WUYI UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

These oxidants catalyze the synthesis of benzimidazoles usually at high temperature, and the conditions are harsh, the operation is complicated, and the post-treatment of the product is cumbersome.
In addition, metal indium compounds, rare earth metal ytterbium compounds, tannic acid, etc. are used as catalysts to synthesize benzimidazole compounds. Although they can effectively catalyze the reaction of o-phenylenediamine and aromatic aldehydes to generate benzimidazole compounds, there are more or less Some problems, such as expensive catalysts, difficult catalyst preparation, harsh reaction conditions, cumbersome post-treatment operations, inability to recycle and reuse catalysts, and hazards of catalyst residues, etc.

Method used

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  • Synthetic method of benzimidazole compounds
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  • Synthetic method of benzimidazole compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A kind of synthetic method of benzimidazole compound, its reaction formula is as follows:

[0033]

[0034] Include the following steps:

[0035] 1) Add o-phenylenediamine (108mg, 1.0mmol), p-chlorobenzaldehyde (141mg, 1.0mmol) and L-carnitine (16.1mg, 0.1mmol) into 5mL of 95% ethanol, heat at 60°C under electromagnetic stirring Reaction 2h, obtain crude product;

[0036] 2) The crude product obtained in step 1) was filtered, dried at 90° C. for 1 h, and recrystallized with ethanol to obtain a white solid with a yield of 97% and a purity of 99%.

[0037] The product is subjected to nuclear magnetic resonance detection and main element analysis, and the data are as follows:

[0038] 1 H-NMR (400MHz, DMSO-d 6 ): δ13.03(s,1H),8.23(d,2H,J=8.5Hz),7.70-7.63(m,3H),7.55(d,1H,J=7.2Hz),7.26-7.23(m, 2H);

[0039] 13 C NMR (100MHz, DMSO-d 6 ): δ149.8, 143.5, 134.5, 134.3, 129.0, 128.7, 128.1, 122.6, 121.8, 118.7, 111.3;

[0040] Anal.Calcd.for C 13 h 9 ClN 2 : C 68.2...

Embodiment 2

[0043] A kind of synthetic method of benzimidazole compound, its reaction formula is as follows:

[0044]

[0045] Include the following steps:

[0046] 1) Add 4-nitro-o-phenylenediamine (153mg, 1.0mmol), p-chlorobenzaldehyde (141mg, 1.0mmol) and L-carnitine (16.1mg, 0.1mmol) into 5mL of 95% ethanol, under electromagnetic stirring , heated at 60°C for 2h to obtain a crude product;

[0047] 2) The crude product obtained in step 1) was filtered, dried at 60° C. for 2 h, and recrystallized with ethanol to obtain a yellow solid with a yield of 98% and a purity of 99%.

[0048] The product is subjected to nuclear magnetic resonance detection and main element analysis, and the data are as follows:

[0049] 1 H-NMR (400MHz, DMSO-d 6 ): δ13.66(s, 1H), 8.81(s, 1H), 8.12(d, J=9.0Hz, 1H), 8.01(d, J=9.0Hz, 1H), 7.52(d, J=9.0Hz ,2H),7.43(d,J=9.0Hz,2H);

[0050] 13 C NMR (100MHz, DMSO-d 6 )δ158.4, 151.1, 135.9, 135.2, 133.3, 131.6, 129.9, 125.0, 124.4, 113.2, 112.8;

[0051] Ana...

Embodiment 3

[0054] A kind of synthetic method of benzimidazole compound, its reaction formula is as follows:

[0055]

[0056] Include the following steps:

[0057] 1) Add o-phenylenediamine (108mg, 1.0mmol), p-methoxybenzaldehyde (136mg, 1.0mmol) and L-carnitine (16.1mg, 0.1mmol) into 5mL of 95% ethanol, under electromagnetic stirring, 60 The reaction was heated at ℃ for 1 h to obtain the crude product;

[0058] 2) The crude product obtained in step 1) was filtered, dried at 70°C for 3 hours, and recrystallized with ethanol to obtain a white solid with a yield of 95% and a purity of 99%.

[0059] The product is subjected to nuclear magnetic resonance detection and main element analysis, and the data are as follows:

[0060] 1 H NMR (400MHz, DMSO-d 6 ): δ12.75(s, 1H), 8.09(d, 2H, J=8.7Hz), 7.55(m, 2H), 7.19-7.16(m, 2H), 7.10(d, 2H, J=8.8Hz) ,3.83(s,3H);

[0061] 13 C NMR (100MHz, DMSO-d 6 ): δ160.3, 151.0, 143.4, 134.7, 127.7, 122.3, 121.8, 121.4, 118.1, 114.0, 110.8, 55.1;

...

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Abstract

The invention discloses a synthetic method of benzimidazole compounds. The synthetic route of the synthetic method is shown in the description. The method comprises the following steps: 1) substitutedo-phenylenediamine (I), aromatic aldehyde (II) and L-carnitine are added to a solvent for a heating reaction, and a crude product is obtained; 2) the crude product obtained in step 1) is filtered, solid substances are collected and dried, and the benzimidazole compounds (III) are obtained, wherein Ar of aromatic aldehyde is a benzene ring with substituents in ortho-position, meta-position and/orpara-position, and the substituents comprise halogen, methoxy and nitro; R of substituted o-phenylenediamine comprises hydrogen and nitro. According to the synthetic method, starting materials are cheap and easily available, reaction conditions are relatively mild, the catalyst L-carnitine is high in catalysis efficiency, postprocessing is simple, the compounds are low-toxic and safe, and industrialization is easy to realize.

Description

technical field [0001] The invention belongs to the field of synthesis of organic heterocyclic compounds, and in particular relates to a synthesis method of benzimidazole compounds. Background technique [0002] Benzimidazole compounds are a very important class of organic heterocyclic compounds, which have a variety of biological and pharmacological activities, such as: blood coagulation, anticancer, antispasmodic, antiallergic, etc. At the same time, benzimidazole derivatives are also many natural An important constituent unit of the product. Therefore, in recent years, people's research on benzimidazole derivatives has become more and more in-depth, and has become a hot spot in the field of organic synthetic chemistry research. [0003] In the prior art, the common method for synthesizing benzimidazole derivatives is to prepare them by dehydration and ring closure of o-phenylenediamine and aromatic aldehyde. Usually strong acid conditions are required, sometimes very hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18
CPCC07D235/18
Inventor 陈路林楚元林振远余林玉张雪芳李亦彪李滨刘强张珉
Owner WUYI UNIV
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