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Method for preparing 2-alkyl imidazole 4,5-dicarboxylic acid

A technology of alkyl imidazole and dicarboxylic acid, applied in the direction of organic chemistry and the like, can solve problems such as difficulty in obtaining raw materials, and achieve the effects of convenient industrial production, good application prospects and little environmental pollution

Inactive Publication Date: 2006-09-13
常州伊思特化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem solved by the present invention is to disclose a new preparation method of 2-alkylimidazole-4,5-dicarboxylic acid, so as to overcome the disadvantages that the raw materials of the existing method are not easy to obtain, and the raw materials used are prepared from highly toxic reagents

Method used

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  • Method for preparing 2-alkyl imidazole 4,5-dicarboxylic acid
  • Method for preparing 2-alkyl imidazole 4,5-dicarboxylic acid
  • Method for preparing 2-alkyl imidazole 4,5-dicarboxylic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Preparation of 2-propylimidazole-4,5-dicarboxylic acid:

[0029] 5.08g of 2-propyl benzimidazole and 0.5g of manganese sulfate were dissolved in 100ml of 40% sulfuric acid. 3 air, O 3 The volume concentration is 1%, O 3 The inflow amount of the product was 80 g, and the reaction was carried out for 5 hours. After the reaction was completed, it was cooled and left to crystallize, and the crude product was obtained by filtration. After purification, it was dried at 80°C to obtain 4.4 g of the title compound.

[0030] Mp: 261-263°C.

[0031] The general reaction formula is as follows:

[0032]

Embodiment 2

[0034] Preparation of 2-methylimidazole-4,5-dicarboxylic acid:

[0035] 15g of 2-methylbenzimidazole and 25g of manganese nitrate were dissolved in 100ml of 40% nitric acid, added hydrogen peroxide with a weight concentration of 25% at 140°C, and reacted for 5 hours. After purification, it was dried at 80°C to obtain 12 g of the title compound.

[0036] The general reaction formula is as follows:

[0037]

Embodiment 3

[0039] Preparation of 2-hexylimidazole-4,5-dicarboxylic acid:

[0040] Dissolve 15g 2-hexylbenzimidazole and 20g manganese chloride in 100ml 30% hydrochloric acid, pass O at 80°C 3 air, O 3 The volume concentration was 8%, and the reaction was carried out for 5 hours. After the reaction was completed, it was cooled and placed to crystallize, and the crude product was obtained by filtration. After purification, it was dried at 80°C to obtain 10 g of the title compound.

[0041] The general formula of the reverse reaction is as follows:

[0042]

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PUM

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Abstract

A process for preparing 2-alkylimidazole-4,5-dicarboxylic acid includes such steps as putting 2-alkyl benzimidazole in solvent, and oxidizing loop-opening reaction under existence of catalyst and oxidant.

Description

technical field [0001] The present invention relates to a preparation method of 2-alkylimidazole-4,5-dicarboxylic acid. Background technique [0002] 2-Alkylimidazole-4,5-dicarboxylic acid is an important pharmaceutical intermediate, especially 2-propylimidazole-4,5-dicarboxylic acid is a new generation of antihypertensive drug Olmesartan. Intermediate. Many documents and patents have disclosed the preparation method of 2-alkylimidazole-4,5-dicarboxylic acid, such as Chinese patent: CN106563A and document: Journal of medicalchemistry, 1996, Nol, 323-33 reported 2-propylimidazole- The preparation method of 4,5-dicarboxylic acid, described method is to make 2-propyl-4,5-dicyano with diaminomaleonitrile and orthobutyric acid triester (trimethyl or triethyl ester) 2-propylimidazole-4,5-dicarboxylic acid is obtained by hydrolysis with hydrochloric acid, and the literatures and patents mentioned above all use the expensive raw materials diaminomaleonitrile and trimethyl orthobut...

Claims

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Application Information

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IPC IPC(8): C07D233/90
Inventor 杨小龙
Owner 常州伊思特化工有限公司
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