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Method for adopting iron-catalyzed N,N-dimethyl-amino-sulfo-formyl chloride derivative for synthesis of benzimidazole derivatives

A technology of dimethylaminothioformyl chloride derivatives and benzimidazole, which is applied in the field of preparation of benzimidazole derivatives, can solve problems such as difficulty in obtaining raw materials, severe reaction conditions, and high toxicity of reagents, and achieves environmental friendliness and easy operation. Simple, Inexpensive Effects

Inactive Publication Date: 2018-07-31
FUJIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The currently reported synthesis methods of benzimidazole compounds have their own advantages and disadvantages, and their use is more or less limited due to the difficulty in obtaining raw materials, the high toxicity of some reagents, the severe reaction conditions and serious environmental pollution.

Method used

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  • Method for adopting iron-catalyzed N,N-dimethyl-amino-sulfo-formyl chloride derivative for synthesis of benzimidazole derivatives
  • Method for adopting iron-catalyzed N,N-dimethyl-amino-sulfo-formyl chloride derivative for synthesis of benzimidazole derivatives
  • Method for adopting iron-catalyzed N,N-dimethyl-amino-sulfo-formyl chloride derivative for synthesis of benzimidazole derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Example 1: 2-(N,N-Dimethylamino)-benzimidazole: Add 1 mmol of o-phenylenediamine to the reaction vessel, add 0.1 mmol of ferric chloride and 1 mmol of cesium carbonate in sequence, N,N -Dimethylcarbamoylthiochloride 2.5 mmol, 3 ml tetrahydrofuran. Heating to 60°C for continuous reaction for 5 h. After the reaction was completed, it was cooled to room temperature, concentrated under reduced pressure, and the product was purified by column chromatography to obtain a white solid with a yield of 87%.

Embodiment 2

[0029] Example 2: 2-(N,N-diethylamino)-benzimidazole: The preparation method is the same as in Example 1, adding 2.5 mmol of N,N-diethylaminothioformyl chloride to obtain a white solid with a yield of 85%.

Embodiment 3

[0030] Example 3: 2-(N,N-di-n-propylamino)-benzimidazole: The preparation method is the same as in Example 1, adding 2.5 mmol of N,N-di-n-propylaminothioformyl chloride to obtain a white solid. Yield 85%.

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Abstract

The invention discloses a method for adopting an iron-catalyzed N,N-dimethyl-amino-sulfo-formyl chloride derivative for synthesis of benzimidazole derivatives. A catalytic quantity of a ferric trichloride catalyst, a cesium carbonate auxiliary catalyst, o-phenylenediamine and o-phenylenediamine derivatives are added into a reaction container, wherein the N,N-dimethyl-amino-sulfo-formyl chloride derivative is adopted as a raw material and tetrahydrofuran is adopted as a solvent for a reaction at certain temperature, a certain time later, pressure is decreased for concentration, and a product issubjected to column chromatography purification. The method is novel in raw material, convenient to operate and efficient and is used for preparing the benzimidazole derivatives. Compared with the prior art, the method has the advantages of being mild in reaction condition, easy to operate, high in yield, safe, low in cost and environmentally friendly. Specific information is shown in the description.

Description

technical field [0001] The invention relates to a method for preparing benzimidazole derivatives. That is, a method for efficiently and rapidly preparing benzimidazole derivatives by using substituted o-phenylenediamine and N,N-dimethylaminothioformyl chloride derivatives as raw materials and anhydrous ferric chloride as a catalyst. Background technique [0002] Benzimidazole is a kind of nitrogen-containing aromatic heterocyclic compound, which is composed of benzene ring and imidazole ring, and is an important pharmacophore. Benzimidazole and its derivatives have good biological activity and reactivity, and are widely used in antibacterial, anticancer, antidiabetic, antiulcer, and antihypertensive aspects, and their synthesis research has far-reaching significance. Recent studies have shown that benzimidazole and its derivatives have good anticoagulant activity, and dabigatran etexilate as a new type of thrombin inhibitor has predictable anticoagulant effect, oral adminis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/30
CPCC07D235/30
Inventor 林小燕林晨许建华柯方张鹏许贻文
Owner FUJIAN MEDICAL UNIV
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