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Pyridine quaternary ammonium salt type halamine antibacterial agent and preparation method thereof

A technology of pyridine quaternary ammonium salt and antibacterial agent, which is applied in the synthesis of pyridine quaternary ammonium salt compounds and the field of antibacterial, can solve problems such as poor water solubility of halamine antibacterial agent, avoid bacterial resistance, easily obtain raw materials, The effect of improving hydrophilicity

Inactive Publication Date: 2015-09-23
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a kind of pyridinium quaternary ammonium salt type haloamine antibacterial agent and preparation method thereof, this antibacterial agent has combined the advantages of pyridinium quaternary ammonium salt antibacterial agent and haloamine antibacterial agent, has solved the problem that the haloamine antibacterial agent is not water-soluble Good question, newer antimicrobial with higher activity

Method used

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  • Pyridine quaternary ammonium salt type halamine antibacterial agent and preparation method thereof
  • Pyridine quaternary ammonium salt type halamine antibacterial agent and preparation method thereof
  • Pyridine quaternary ammonium salt type halamine antibacterial agent and preparation method thereof

Examples

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Embodiment 1

[0022] Dissolve 5,5-dimethylhydantoin (3.026g, 23.6mmol) in 200mL acetone, stir to dissolve, add anhydrous K 2 CO 3 (12.050g, 87.2mmol), refluxed for 30min, then added 1,3-dibromopropane (7mL, 68.7mmol) to the mixture, continued to reflux for 4h to obtain a white suspension, and removed the solvent to obtain a white solid. Add 100mL of water and 100mL of ethyl acetate to it for extraction and liquid separation, take the upper layer liquid, remove the solvent and perform column chromatography, using ethyl acetate / petroleum ether as eluent. The resulting liquids containing the product were pooled, and the white solid obtained after removal of the solvent was the bromoalkylhydantoin compound (5.048 g, 85.8%).

[0023] Bromoalkylhydantoin compound (3.091g, 12.4mmol) was dissolved in 50mL of solvent acetonitrile, and excess pyridine (3.015mL, 37.4mmol) was added, heated to reflux overnight, and column chromatography was carried out after removing the solvent. Methane was used as ...

Embodiment 2

[0028] Dissolve 5,5-dimethylhydantoin (3.240g, 25.3mmol) in 200mL acetone, stir to dissolve, add anhydrous K 2 CO 3 (13.771g, 101.2mmol), refluxed for 30min, then added 1,3-dibromododecane (24.907g, 75.9mmol) to the mixture, continued to reflux for 24h to obtain a white suspension, and removed the solvent to obtain a white solid. Add 100mL of water and 100mL of ethyl acetate to it for extraction and liquid separation, take the upper layer liquid, remove the solvent and perform column chromatography, using ethyl acetate / petroleum ether as eluent. The resulting liquids containing the product were pooled, and the white solid obtained after removal of the solvent was the bromoalkylhydantoin compound (6.682 g, 70.4%).

[0029] Bromoalkylhydantoin compound (2.133g, 5.7mmol) was dissolved in 40mL of solvent acetonitrile, and excess pyridine (1.362g, 1.4mL, 17.1mmol) was added, heated to reflux overnight, and column chromatography was carried out after solvent removal, and methanol ...

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Abstract

The invention discloses a pyridine quaternary ammonium salt type halamine antibacterial agent with a structure represented by a general formula I, wherein n is an integer of 1-10. The preparation method comprises the following steps: a, 5,5-dimethyl hydantoin is placed in an acetone solution doped with anhydrous potassium carbonate; refluxing is carried out for 30min, and dibromoalkane is added; refluxing is continued for 4h, such that a bromo-alkyl hydantoin compound is obtained; b, the obtained bromo-alkyl hydantoin compound is dissolved in acetonitrile; excessive pyridine is added; heating and refluxing are carried out overnight; concentration is carried out, such that a pyridine bromide quaternary ammonium salt type halamine precursor is obtained; the precursor is delivered through chlorine-type anion exchange resin, such that a pyridine chloride quaternary ammonium salt type halamine precursor is obtained; and c, the obtained pyridine chloride quaternary ammonium salt type halamine precursor is dissolved in a mixed solution composed of deionized water and tert-butanol; tert-butyl hypochlorite is added, and stirring is carried out for 2-4h while protected from light, such that the pyridine quaternary ammonium salt type halamine is obtained. The method has the advantages of easy-to-obtain raw materials, and relatively simple synthesis method. The method has a prospect of industrialized application.

Description

technical field [0001] The invention relates to a class of halogenated amine antibacterial agents containing a pyridine quaternary ammonium salt structure and a preparation method thereof, belonging to the technical field of synthesis and antibacterial pyridine quaternary ammonium salt compounds. Background technique [0002] For nearly half a century, with the continuous deterioration of the environment, pathogenic microorganisms have spread widely, leading to frequent public safety incidents. For example, the pathogenic Escherichia coli, SARS virus, avian influenza virus, and Ebola virus that have been popular in recent years have all caused great threats to people's lives and lives and property. Therefore, antibacterial reagents and antibacterial material products have received more and more attention. Making antibacterial agents into antibacterial materials and applying them in food, water treatment, medical and health fields can effectively reduce the influence of path...

Claims

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Application Information

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IPC IPC(8): C07D401/06A01N43/50A01P1/00A61P31/04
CPCC07D401/06A01N43/50
Inventor 李令东陈洪媛闫超
Owner DALIAN UNIV OF TECH
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