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2,2'-(1,4-phenylene)bi(benzimidazole-5-carboxylic acid) and preparation method thereof

A technology of benzimidazole and phenylene, applied in the field of new compounds and their preparation, can solve problems such as difficult separation, and achieve the effect of high utilization rate of raw materials

Inactive Publication Date: 2010-06-16
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since terephthalic acid and 3,4-diaminobenzoic acid have similar reactivity to the carboxyl group, 3,4-diaminobenzoic acid has a side reaction of self-condensation, and the product is a complex mixture that is difficult to separate

Method used

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  • 2,2'-(1,4-phenylene)bi(benzimidazole-5-carboxylic acid) and preparation method thereof
  • 2,2'-(1,4-phenylene)bi(benzimidazole-5-carboxylic acid) and preparation method thereof
  • 2,2'-(1,4-phenylene)bi(benzimidazole-5-carboxylic acid) and preparation method thereof

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Effect test

Embodiment 1

[0042] Example 1 The preparation of 2,2'-(1,4-phenylene)bis(benzimidazole-5-carboxylic acid)

[0043] 12.4mmol 3,4-diaminobenzoic acid, 10mL dimethyl sulfoxide, heated in an oil bath, raised the temperature to 80°C, added dropwise 6.2mmol terephthalaldehyde in dimethyl sulfoxide solution, stirred for 2.0h, and added to the reaction system Add 4.2mmol of 3-nitro-4-aminobenzoic acid, continue stirring for 2.0h; pour the reaction liquid into 80mL of ethanol, let it stand, filter, and dry to obtain a light brown solid with a yield of 94.6%, mp.≥300°C.1 HNMR (400MHz, DMSO-d 6 ), δ: 7.84~8.29(m, 6H, 2×C 6 h 3 ), 8.41(s, 4H, C 6 h 4 ), 12.78(s, 2H, 2×NH), 13.40(s, 2H, 2×CO 2 H); IR (KBr, cm -1 )υ: 3367 (broad peak, O-H, N-H), 3212 (Ph-H), 1677, 1624 (C=O, C=N), 1543 (Ph), 1322, 1306, 1016, 963 (Ph). Recover 3,4-diaminobenzoic acid as a raw material.

Embodiment 2

[0044] Example 2 Preparation of 2,2'-(1,4-phenylene)bis(benzimidazole-5-carboxylic acid)

[0045] 12.4mmol 3,4-diaminobenzoic acid, 10mL acetonitrile, heated in an oil bath, raised the temperature to 80°C, added dropwise 6.2mmol terephthalaldehyde acetonitrile solution, stirred for 1.5h, added 4.2mmol 3-amino- 4-Nitrobenzoic acid, continue to stir and react for 2.0 h; the reaction solution is poured into 80 mL of ethanol, allowed to stand, filtered, and dried to obtain a light brown solid with a yield of 94.3%, mp.≥300°C. 1 H NMR (400MHz, DMSO-d 6 ), δ: 7.84~8.29(m, 6H, 2×C 6 h 3 ), 8.41(s, 4H, C 6 h 4 ), 12.78(s, 2H, 2×NH), 13.40(s, 2H, 2×CO 2 H); IR (KBr, cm -1 )υ: 3367 (broad peak, O-H, N-H), 3212 (Ph-H), 1677, 1624 (C=O, C=N), 1543 (Ph), 1322, 1306, 1016, 963 (Ph). Recover 3,4-diaminobenzoic acid as a raw material.

Embodiment 3

[0046] Example 3 Preparation of 2,2'-(1,4-phenylene)bis(benzimidazole-5-carboxylic acid) (cerium ammonium nitrate-hydrogen peroxide composite oxidation method)

[0047] 12.4mmol 3,4-diaminobenzoic acid, 10mL N,N-dimethylformamide, heated in an oil bath, raised to 80°C, added dropwise 6.2mmol terephthalaldehyde N,N-dimethylformamide solution, Stir the reaction for 1 hour, cool down to 60°C, add 0.67g of cerium ammonium nitrate and 5mL of 30% hydrogen peroxide to the reaction system, and continue to stir and react for 20 minutes; the reaction solution is poured into 80mL of ethanol, left to stand, filtered, and dried to obtain 2.34g of light brown Solid, yield 94.7%, mp.≥300°C. 1 H NMR (400MHz, DMSO-d 6 ), δ: 7.84~8.29(m, 6H, 2×C 6 h 3 ), 8.41(s, 4H, C 6 h 4 ), 12.78(s, 2H, 2×NH), 13.40(s, 2H, 2×CO 2 H); IR (KBr, cm -1 )υ: 3367 (broad peak, O-H, N-H), 3212 (Ph-H), 1677, 1624 (C=O, C=N), 1543 (Ph), 1322, 1306, 1016, 963 (Ph).

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Abstract

The invention discloses 2,2'-(1,4-phenylene)bi(benzimidazole-5-carboxylic acid) which has the following structural formula and a preparation method thereof. The preparation method comprises the steps of: dissolving 3,4-diaminobenzoic acid in an aprotic polar solvent, heating by using an oil bath to a certain temperature, dropwise adding an aprotic polar solvent solution of terephthalaldehyde, stirring for a certain time after the adding; adding an oxidant in a reaction system, and continuously stirring for reacting for a certain time; and pouring reaction liquid into alcohol, filtering, and drying to obtain a light brown solid (2,2'-(1,4-phenylene)bi(benzimidazole-5-carboxylic acid)). The aprotic polar solvent is selected from one or more of tetrahydrofuran, acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide and dimethylsulfoxide; and the oxidant is selected from one or more of cerous nitrate, hydrogen peroxide, ferric trichloride, copper acetate, iodobenzene diacetate, air, oxygen, benzoquinone, dichloro dicyane benzoquinone and 3-nitryl-4-aminobenzoic acid.

Description

technical field [0001] The present invention relates to a new compound and its preparation method, specifically 2,2'-(1,4-phenylene)bis(benzimidazole-5-carboxylic acid) and its preparation method. Background technique [0002] Bisbenzimidazole derivatives are widely used in many fields such as medicine, chemical engineering and biology [J Appl SurSci, 2006, 252(23): 8178]. In the field of medicine, bisbenzimidazole compounds have important medicinal value in anti-cancer, anti-fungal, analgesic, anti-inflammatory, anti-rheumatic, etc. For example, APC-6336 has a good inhibitory effect on the activity of HCV NS3 / NS4 enzymes Effect [J Bioorg Med Chem Lett, 2001, 11(17): 2355]. Bis(5-amidino-2-benzimidazole)methane can effectively inhibit the activity of serine protease [J Mol Biol, 1999, 292(3): 669], and has certain curative effect on malignant tumors [J Med Chem, 1993, 36 (12): 1746]. Due to the special structure, bis(substituted benzimidazole)methane derivatives also have...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/20
Inventor 陈平石磊刘祈星胡艾希
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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