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Synthesizing process of benzimidazole-2-formaldehyde

A technology for the synthesis of benzimidazole and benzimidazole derivatives, which is applied in the field of synthesis of benzimidazole derivatives, can solve problems such as inapplicability, and achieve the effects of low cost, favorable operation safety, energy saving, and mild reaction conditions

Active Publication Date: 2015-12-30
上海泰坦科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although the above-mentioned prior art discloses a synthetic method of 2-substituted benzimidazole derivatives, in the process of realizing the present invention, the inventor finds that the technical scheme of the above-mentioned prior art cannot be directly applied to benzo Synthesis of imidazole-2-carbaldehyde

Method used

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  • Synthesizing process of benzimidazole-2-formaldehyde

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Comparison scheme
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Embodiment 1

[0015] This embodiment relates to a synthesis process of benzimidazole-2-carbaldehyde, which consists of the following steps:

[0016] 200 mesh hydroxyapatite powder 0.008mol as a catalyst, 52℃ hot water 100mL as a solvent, 0.1mol o-phenylenediamine and 0.11mol glyoxylic acid as raw materials for the reaction, the reaction time is 6 hours, the reaction temperature is 52 After the reaction is over, filter while hot and cool the filtrate to 2°C. White crystals are precipitated. The crystals are obtained by filtration and dried in vacuum at 35°C overnight to obtain 11.9 g of benzimidazole-2-carbaldehyde, yield 81%, purity 99.6%, MS: m / z=146(M + ), 1 HNMR (DMSO, 500MHz) δ: 11.03 (s, 1H), 10.15 (s, 1H), 8.24 (d, J = 8.4 Hz, 1H), 8.01 (d, J = 8.5 Hz, 1H), 7.65-7.58 ( m,2H).

Embodiment 2

[0018] Using 0.001 mol of 200 mesh hydroxyapatite powder as a catalyst, 100 mL of hot water at 46°C as a solvent, and 0.1 mol o-phenylenediamine and 0.12 mol glyoxylic acid as raw materials for the reaction. The reaction time is 10 hours and the reaction temperature is 46. After the reaction is completed, filter while hot and cool the filtrate to 4°C. White crystals are precipitated. The crystals are obtained by filtration and dried under vacuum at 35°C overnight to obtain 11.6 g of benzimidazole-2-carboxaldehyde, with a yield of 79% and purity. 99.2%, MS: m / z=146(M + ), 1 HNMR (DMSO, 500MHz) δ: 11.02 (s, 1H), 10.19 (s, 1H), 8.24 (d, J = 8.5 Hz, 1H), 8.03 (d, J = 8.5 Hz, 1H), 7.66-7.54 ( m,2H).

Embodiment 3

[0020] 0.02 mol of 200 mesh hydroxyapatite powder was used as a catalyst, 100 mL of hot water at 58°C was used as a solvent, and 0.1 mol o-phenylenediamine and 0.1 mol glyoxylic acid were used as raw materials for the reaction. The reaction time was 2 hours and the reaction temperature was 58. After the reaction is over, filter while hot and cool the filtrate to 0°C. White crystals are precipitated. The crystals are obtained by filtration and dried under vacuum at 35°C overnight to obtain 11.5 g of benzimidazole-2-carboxaldehyde, yield 78%, purity 98.9%, MS: m / z=146(M + ), 1 HNMR (DMSO, 500MHz) δ: 11.04 (s, 1H), 10.17 (s, 1H), 8.24 (d, J = 8.5 Hz, 1H), 8.02 (d, J = 8.6 Hz, 1H), 7.62-7.58 ( m,2H).

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Abstract

The invention relates to a synthesizing process of benzimidazole-2-formaldehyde. The synthesizing process comprises the following steps: hydroxyapatite powder is taken as a catalyst, hot water with the temperature of 46 DEG C to 58 DEG C is taken as a solvent, o-phenylenediamine and glyoxylic acid are taken as raw materials for reaction, the molar ratio of the o-phenylenediamine and the glyoxylic acid is 1:(1-1.2), the reaction time is 2-10 h, the reaction temperature is 46 DEG C to 58 DEG C, after the reaction, filtrate is cooled to the temperature of 0 DEG C to 4 DGE C while the solution is hot, white crystals are precipitated, and crystals are obtained through filtration and dried, so that the benzimidazole-2-formaldehyde is obtained. According to the synthesizing process, the raw materials and the catalyst are easy to obtain, and the cost is low; 100 DEG C is not required in the operation steps, and the reaction condition of 46 DEG C to 58 DEG C is relatively mild; the target object of the benzimidazole-2-formaldehyde can be obtained by post-process through filtration, cooling and re-filtration, the operation is simple, and accordingly, the synthesizing process is suitable for industrial large-scale synthesis of the benzimidazole-2-formaldehyde.

Description

Technical field [0001] The invention relates to a synthesis process of benzimidazole derivatives, in particular to a synthesis process of benzimidazole-2-carbaldehyde. Background technique [0002] Benzimidazole compounds are benzoheterocyclic compounds containing two nitrogen atoms. Benzimidazole derivatives and their metal complexes have good biological activity and can be used as pharmaceutical intermediates to prepare insect repellents for humans and animals. , Benzimidazole and its derivatives containing imidazole ring have very important medicinal value in anti-cancer, anti-fungal, analgesic and anti-inflammatory, anti-rheumatism, and deworming due to their special structure, physiological activity and reactivity. , The application is very wide, therefore, the synthesis and application research of benzimidazole and its derivatives have never stopped for decades, and it is still very active. Due to the excellent characteristics and wide application of benzimidazole derivati...

Claims

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Application Information

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IPC IPC(8): C07D235/12
CPCC07D235/12
Inventor 谢应波张庆张华徐肖冰罗桂云
Owner 上海泰坦科技股份有限公司