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6-flourine-3a-(trifluoromethyl)-2,3,3a,4-tetrahydro-1h-benzo[d]pyrrole[1,2-a]imidazole-1-ketone and method for synthesizing same

A technology of trifluoromethyl and p-toluenesulfonic acid, applied to 6-fluoro-3a-(trifluoromethyl)-2, can solve problems such as unreported

Inactive Publication Date: 2009-09-30
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The synthesis method of this compound has not been reported yet

Method used

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  • 6-flourine-3a-(trifluoromethyl)-2,3,3a,4-tetrahydro-1h-benzo[d]pyrrole[1,2-a]imidazole-1-ketone and method for synthesizing same
  • 6-flourine-3a-(trifluoromethyl)-2,3,3a,4-tetrahydro-1h-benzo[d]pyrrole[1,2-a]imidazole-1-ketone and method for synthesizing same
  • 6-flourine-3a-(trifluoromethyl)-2,3,3a,4-tetrahydro-1h-benzo[d]pyrrole[1,2-a]imidazole-1-ketone and method for synthesizing same

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Experimental program
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Effect test

Embodiment 1

[0030] Embodiment 1: 1. add 0.44 grams of trifluoro γ-keto acid methyl esters, 0.019 grams of p-toluenesulfonic acid, 25 milliliters of toluene, 0.2 grams of anhydrous magnesium sulfate in 50 milliliters of round bottom flasks that reflux condenser tube is housed . The above mixture was stirred and refluxed in an oil bath for half an hour, and then 0.252 g of p-fluoro-o-phenylenediamine was added; ② The reactant gradually turned yellow under reflux. After 12 hours of reaction, 0.019 g of p-toluenesulfonic acid was added. The reaction was continued for 12 hours and then stopped. After the reaction was completed, anhydrous magnesium sulfate was removed by suction filtration, and the filtrate was concentrated. ③ The obtained concentrated solution was separated by silica gel chromatography, and the developer was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 4:1 to obtain 0.31 g of a white solid with a yield of 58%.

Embodiment 2

[0031] Embodiment 2: 1. add 11 grams of methyl trifluoro γ-keto acids in a 250 milliliter round-bottomed flask equipped with a reflux condenser, 0.475 grams of p-toluenesulfonic acid, 150 milliliters of toluene, and 5 grams of anhydrous magnesium sulfate . The above mixture was stirred and refluxed in an oil bath for half an hour, and then 6.3 g of p-fluoro-o-phenylenediamine was added; ② The reactant gradually turned yellow under reflux. After 12 hours of reaction, 0.475 g of p-toluenesulfonic acid was added. The reaction was continued for 16 hours and then stopped. After the reaction was completed, anhydrous magnesium sulfate was removed by suction filtration, and the filtrate was concentrated. ③ The obtained concentrated solution was separated by silica gel chromatography, and the developer was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 4:1 to obtain 7.28 g of a white solid with a yield of 56%.

Embodiment 3

[0032] Embodiment 3: 1. add 110 grams of trifluoro γ-keto acid methyl esters, 4.75 grams of p-toluenesulfonic acid, 1000 milliliters of toluene, 25 grams of anhydrous magnesium sulfate in 2 liters of round-bottomed flasks equipped with a reflux condenser . The above mixture was stirred and refluxed in an oil bath for half an hour, and then 63 g of p-fluoro-o-phenylenediamine was added. ② The reaction product gradually turned yellow under reflux. After 12 hours of reaction, 4.75 g of p-toluenesulfonic acid was added. The reaction was continued for 20 hours and then stopped. After the reaction was completed, anhydrous magnesium sulfate was removed by suction filtration, and the filtrate was concentrated. ③ The obtained concentrated solution was separated by silica gel chromatography, and the developer was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 4:1 to obtain 70.2 g of a white solid with a yield of 54%.

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Abstract

The invention relates to a 6-flourine-3a-(trifluoromethyl)-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrole[1,2-a]imidazole-1-ketone and a method for synthesizing the same. The structural formula of the compound is shown as a right formula. The method comprises the following steps that: trifluoro gamma-keto acid methyl ester and toluene sulfonic acid are dissolved in toluene and added with anhydrous magnesium sulfate in catalyst amount, and the mixture is subjected to refluxing reaction for 20 to 60 minutes in stirring, and then added with fluorine o-phenylendiamine; the mixture is continuously reacted for 10 to 15 hours and then added with toluene sulfonic acid in catalyst amount; the mixture is subjected to refluxing reaction for 10 to 15 hours; after the reaction, the mixture is separated and purified to obtain a white solid which is the 6-flourine-3a-(trifluoromethyl)-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrole[1,2-a]imidazole-1-ketone; and the molar ratio of the trifluoro gamma-keto acid methyl ester to the fluorine o-phenylendiamine is 1-1.2:1. The 6-flourine-3a-(trifluoromethyl)-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrole[1,2-a]imidazole-1-ketone has stronger activity and is absorbed more easily. Moreover, the method has the advantages of easily bought raw materials, quite simple operation, synthesis by a one-pot method, 58 percent of yield and suitability for mass production.

Description

Technical field: [0001] The present invention relates to a 3'-trifluoromethyl-1-fluorobenzimidazole pyrrolone derivative and its synthesis method, especially a 6-fluoro-3a-(trifluoromethyl)-2,3, 3a,4-Tetrahydro-1H-benzo[d]pyrrole[1,2-a]imidazol-1-one and its synthesis method. Background technique: [0002] Nitrogen-containing heterocyclic compounds are widely used not only in pesticides but also in medicine, so they are a very important class of organic compounds. In recent decades, scientists have continuously explored its new synthesis process, and conducted a lot of research on its structure and properties. [0003] As an important nitrogen-containing heterocyclic compound, benzimidazoles have been widely used and studied in recent years. Not only can it be used as a drug with low toxicity and high efficiency, but its polymer can also be used as a high temperature resistant composite material. Pyrrolidone compounds are also a class of compounds with high application va...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
Inventor 郝健侯明华庄红伟万文蒋海珍
Owner SHANGHAI UNIV
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