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Method for synthesizing bis-benzimidazole compound through one-pot method

A technology for bisbenzimidazole and compound is applied in the field of synthesizing bisbenzimidazole compounds, and can solve the problems of inapplicable bisbenzimidazoles, low yield, poor activity and selectivity of bisbenzimidazoles, etc. To achieve the effect of convenient product separation, convenient industrial production and good stability

Active Publication Date: 2016-07-20
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this reaction system is not suitable for the synthesis of bis-benzimidazoles. There are two main reasons: ① the solubility of the raw material bis-o-nitroanilines in the reaction system is extremely poor, so the synthesis efficiency is low; ② solid catalyst Cu-Zn-Pd / Al 2 o 3 The activity and selectivity in this reaction system are all poor, cause the yield of target product bisbenzimidazoles compound to be low

Method used

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  • Method for synthesizing bis-benzimidazole compound through one-pot method
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  • Method for synthesizing bis-benzimidazole compound through one-pot method

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Take 10g specific surface area as 250m 2 g -1 , average pore size 8nm, particle size 500 mesh γ-Al 2 o 3 Add water and stir, heat in a water bath to 60°C, add 10mL of H 2 PdCl 4 solution (Pd content is 0.05g / mL), 10mLMg(NO 3 ) 2 solution (Mg content is 0.03g / mL) and 10mL Cu(NO 3 ) 2 Solution (Cu content is 0.05g / mL), kept at 60°C for 4 hours, added dropwise NaOH solution to adjust the pH value to 8-10, kept the solution temperature and stirred for 1 hour; filtered, and the filter cake was washed with deionized water to medium properties; vacuum drying at 100°C for 5h; then, calcining at 300°C for 4h, and finally reducing with hydrogen at 300°C for 4h to obtain Cu5wt%-Mg3wt%-Pd5wt% / γ-Al 2 o 3 catalyst.

Embodiment 2

[0035] Take 10g specific surface area as 350m 2 g -1 , average pore size 10nm, particle size 800 mesh γ-Al 2 o 3 Add water and stir, heat in a water bath to 80°C, add dropwise 10mL of Pt(NO 3 ) 2 solution (Pt content is 0.08g / mL), 10mLBaCl 2 solution (Ba content is 0.02g / mL) and 10mL CuCl 2 Solution (Cu content is 0.02g / mL), kept at 80 ℃ for 4 hours, added dropwise (NH 4 ) 2 CO 3 Adjust the pH value of the solution to between 8 and 10, keep the solution temperature and stir for 3 hours; filter, wash the filter cake with deionized water until neutral; vacuum dry at 105°C for 4h; then, roast at 260°C for 8h, and finally in Reduction with hydrogen at 300°C for 5 hours to obtain Cu2wt%-Ba2wt%-Pt8wt% / γ-Al with corresponding loading 2 o 3 catalyst.

Embodiment 3

[0037] Take 10g specific surface area as 450m 2 g -1 , average pore size 20nm, particle size 800 mesh γ-Al 2 o 3 Add water and stir, heat in a water bath to 90°C, add 10mL of H 2 PtCl 6 solution (Pt content is 0.03g / mL), 10mL Pd(C 2 h 3 o 2 ) 2 Solution (Pd content is 0.03g / mL), 10mLKNO 3 solution (K content is 0.04g / mL) and 10mL Cu(NO 3 ) 2 Solution (Cu content: 0.03g / mL), kept at 90°C for 8 hours, added KOH solution dropwise to adjust the pH value to 8-10, kept the solution temperature and stirred for another 2 hours; filtered, and the filter cake was washed with deionized water to medium properties; vacuum drying at 110°C for 8h; then calcination at 400°C for 5h, and finally reduction with hydrogen at 350°C for 3h to obtain Cu3wt%-K4wt%-Pd3wt%-Pt3wt% / γ-Al 2 o 3 catalyst.

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Abstract

The invention provides a method for synthesizing a bis-benzimidazole compound through a one-pot method.According to the method, a bis(ortho-nitroaniline) compound shown in a formula II-1 or II-2 or II-3 and alcohol shown in a formula III are used as raw materials, water and organic solvent are added, and under the effect of a load type multi-metal solid catalyst, the bis-benzimidazole compound shown in the corresponding formula II-1 or II-2 or II-3 is synthesized through the one-pot method, wherein X1, X2, X3, X4, X5, X6, X7 and X8 are H, F, C1, CH3, CH2CH3 and OCH3 or OCH2CH3 independently; X9 is O or CO or CH2 or NH; R1 is H or alkyl or phenyl or alkyl phenyl or alkoxy phenyl, and the number of carbon atoms of alkyl and alkoxy is 1-3; in Y1 and Y2, Y3 and Y4, Y5 and Y6, Y7 and Y8, Y9 and Y10, and Y11 and Y12, one in each group is amino, and the other in each group is nitryl.The method has the advantages that the synthetic route technology is simple, the product yield is high, the production cost is low, the catalyst is easy to separate, high in activity and good in stability, and liquid acid is not used.

Description

technical field [0001] The invention relates to a method for synthesizing bisbenzimidazole compounds. Background technique [0002] Bisbenzimidazole compounds are an important class of pharmaceutical and material intermediates, which can be used to synthesize antiviral drugs and high-performance composite materials. [0003] The traditional method for synthesizing bis-benzimidazoles is to prepare the corresponding bis-o-phenylenediamine and acid anhydride, aldehyde or acid chloride as raw materials under the action of a catalyst. For example, the literature [SaeedBahadoriKhalili, AliRezaSardarian, Monatsh.Chem., 2012,143:841-846] reports a kind of raw material with 3,3'-diamino-p-diaminobiphenyl and acid chloride or acid anhydride, with KF / Al 2 o 3 As catalyst, anhydrous MgSO 4 As an auxiliary agent, 2,2'-substituted bisbenzimidazoles were prepared with a yield of 70-79%; however, the literature pointed out that all reagents in the reaction must be anhydrous, and a large ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/06C07D235/08C07D235/18C07D487/04B01J23/89
CPCB01J23/8926C07D235/06C07D235/08C07D235/18C07D487/04
Inventor 张群峰丰枫许孝良程正马磊卢春山李小年
Owner ZHEJIANG UNIV OF TECH
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