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Catalyst-free method for preparing imidazole or benzothiazole type compounds

A technology of benzimidazole and benzothiazole, which is applied in the field of preparation of benzimidazoles or benzothiazoles, can solve problems such as long reaction time, and achieves the effects of easy operation, mild conditions, and obvious industrial application prospects.

Inactive Publication Date: 2016-04-20
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

That is, in the prior art, the reaction system needs to use catalysts, organic solvents or special reaction conditions such as microwaves, and the reaction time is long.

Method used

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  • Catalyst-free method for preparing imidazole or benzothiazole type compounds
  • Catalyst-free method for preparing imidazole or benzothiazole type compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Embodiment 1 Synthetic 2-Methylbenzimidazole

[0014] Add 0.5 mmol of o-phenylenediamine, 0.75 mmol of acetylacetone, and 2 mL of water into the reaction flask in sequence, and react at 100° C. for 2 hours. After the reaction, 10 mL of saturated brine was added, the reaction mixture was extracted three times with 15 mL of ethyl acetate, the organic phases were combined, concentrated, and separated by column chromatography to obtain 2-methylbenzimidazole with a separation yield of 98%.

Embodiment 2

[0015] Embodiment 2 Synthetic 2-Methylbenzimidazole

[0016] Add 0.5 mmol of o-phenylenediamine, 0.75 mmol of acetylacetone, and 5 mL of water into the reaction flask in sequence, and react at 100° C. for 2 hours. After the reaction, 10 mL of saturated brine was added, the reaction mixture was extracted three times with 15 mL of ethyl acetate, the organic phases were combined, concentrated, and separated by column chromatography to obtain 2-methylbenzimidazole with an isolation yield of 96%.

Embodiment 3

[0017] Embodiment 3 Synthetic 2-Methylbenzimidazole

[0018] Add 0.5 mmol of o-phenylenediamine, 1.0 mmol of acetylacetone, and 2 mL of water into the reaction flask in sequence, and react at 100° C. for 2 hours. After the reaction, 10 mL of saturated brine was added, the reaction mixture was extracted three times with 15 mL of ethyl acetate, the organic phases were combined, concentrated, and separated by column chromatography to obtain 2-methylbenzimidazole with a separation yield of 98%.

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Abstract

The invention provides a catalyst-free method for preparing imidazole or benzothiazole type compounds, and belongs to the technical field of organic synthesis. According to the method, imidazole or benzothiazole type compounds are efficiently prepared by making o-phenylenediamine type compounds or aminothiophenol type compounds react with diketone compounds in water or air. The method has the advantages that no catalysts or additives are needed, the reaction can happen in a single water phase, use of catalysts, various additives and toxic organic solvent is avoided, and the reaction system is green and efficient and is a good system for preparing imidazole and benzothiazole type compounds.

Description

technical field [0001] The invention relates to a method for preparing benzimidazole or benzothiazole compounds in water and air without catalyst and any additives, which belongs to the technical field of organic synthesis. Background technique [0002] Benzimidazole and benzothiazole compounds are important drug intermediates, which are widely used in the fields of pesticides and medicine, and are used to synthesize anti-HIV virus, anti-cancer, antibacterial and plant viruses (Chin.J.Pestic.2000 , 39, 1; Pharm.Chem.J.2000, 34, 353; Bioorg.Med.Chem.Lett.2002, 12, 3275; Med.Chem.Lett.2003, 13, 471; ; J. Med. Chem. 2012, 55, 2981). The reaction of o-phenylenediamine compounds or o-aminobenzenethiol compounds and diketones is an effective method for the synthesis of benzimidazoles and benzothiazoles (Org.Lett.2014,16,764; J.HeterocyclicChem.2005 ,42,1001). In patent CN103910682A, o-phenylenediamine compounds are used to prepare benzimidazole, protonic acid is used as catalys...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/08C07D277/64
CPCC07D235/08C07D277/64
Inventor 刘春王会会
Owner DALIAN UNIV OF TECH