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7-chlorine-3a-(trifluoromethyl)-3, 3a-dihydrobenzo (d) pyrrole (2, 1-b)-oxazole-1(2H)-ketone and synthetic method thereof

A technology of trifluoromethyl and dihydrobenzene, applied in 7-chloro-3a-(trifluoromethyl)-3

Inactive Publication Date: 2009-09-16
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthesis method of this compound has not been reported yet

Method used

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  • 7-chlorine-3a-(trifluoromethyl)-3, 3a-dihydrobenzo (d) pyrrole (2, 1-b)-oxazole-1(2H)-ketone and synthetic method thereof
  • 7-chlorine-3a-(trifluoromethyl)-3, 3a-dihydrobenzo (d) pyrrole (2, 1-b)-oxazole-1(2H)-ketone and synthetic method thereof
  • 7-chlorine-3a-(trifluoromethyl)-3, 3a-dihydrobenzo (d) pyrrole (2, 1-b)-oxazole-1(2H)-ketone and synthetic method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Example 1: ①In a 50 ml round-bottomed flask equipped with a reflux condenser, add 0.44 g of methyl trifluoroγ-ketoate, 0.019 g of p-toluenesulfonic acid, 25 ml of toluene, and 0.2 g of anhydrous magnesium sulfate . The above mixture was stirred and refluxed in an oil bath for half an hour, and then 0.287 g of 2-amino-4-chlorophenol was added; ② the reaction solution gradually turned red 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, the 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 developing solvent was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 6:1 to obtain 0.38 g of an off-white solid with a yield of 68%.

Embodiment 2

[0030] Example 2: ① In a 250 ml round-bottomed flask equipped with a reflux condenser, add 11 g of methyl trifluoroγ-ketoate, 0.475 g of p-toluenesulfonic acid, 150 ml of toluene, and 5 g of anhydrous magnesium sulfate . The above mixture was stirred and refluxed in an oil bath for half an hour, and then 7.25 g of 2-amino-4-chlorophenol was added; ② the reaction solution gradually turned red under reflux. After 12 hours of reaction, 0.475 g of p-toluenesulfonic acid was added. The reaction was continued for 24 hours and then stopped. After the reaction was completed, the 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 developing solvent was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 6:1 to obtain 9.14 g of an off-white solid with a yield of 66%.

Embodiment 3

[0031] Example 3: ① In a 2-liter round-bottomed flask equipped with a reflux condenser, add 110 grams of methyl trifluoroγ-ketoate, 4.75 grams of p-toluenesulfonic acid, 1000 milliliters of toluene, and 20 grams of anhydrous magnesium sulfate. . The above mixture was stirred and refluxed in an oil bath for half an hour, and then 72.5 g of 2-amino-4-chlorophenol was added. ② The reactant gradually turned red under reflux. After 12 hours of reaction, 4.75 g of p-toluenesulfonic acid was added. The reaction was continued for 32 hours and then stopped. After the reaction was completed, the 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 developing solvent was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 6:1 to obtain 87.3 g of an off-white solid with a yield of 63%.

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Abstract

The invention relates to a 7-chlorine-3a-(trifluoromethyl)-3, 3a-dihydrobenzo (d) pyrrole (2, 1-b)-oxazole-1(2H)-ketone and a synthetic method thereof. The structural formula of the compound is shown as the right formula; the method comprises the following steps: trifluoro-gama-methyl ketonic acid and p-toluene sulfonic acid with the amount of a catalyst are dissolved in methylbenzene, anhydrous magnesium sulfate with the amount of the catalyst is added, reflux is carried out for 20 to 60 minutes under stirring and then 2-amino-4-chlorophenol is added; the obtained mixture continuously reacts for 10 to 15 hours, and then p-toluene sulfonic acid with the amount of the catalyst is added and reflux reaction is carried out for 10 to 15 hours; the molar ratio of trifluoro-gama-methyl ketonic acid to 2-amino-4-chlorophenol is (1-1.2):1, and then reaction is ended; and off-white solid is obtained by separation and purification, namely 7-chlorine-3a-(trifluoromethyl)-3, 3a-dihydrobenzo (d) pyrrole (2, 1-b)-oxazole-1(2H)-ketone. The 7-chlorine-3a-(trifluoromethyl)-3, 3a-dihydrobenzo (d) pyrrole (2, 1-b)-oxazole-1(2H)-ketone has stronger activity and is more beneficial to being absorbed. The invention has easily obtained raw materials and very simple operation, adopts one-pot synthesis, has productivity up to 68 percent and is applicable to production on large scale.

Description

Technical field: [0001] The present invention relates to a 7-chloro-3a-(trifluoromethyl)-3,3a-dihydrobenzo[d]pyrrole[2,1-b]oxazol-1(2H)-one and its synthesis method. Background technique: [0002] Heterocyclic chemistry has always been an important research hotspot because of the close relationship between heterocyclic chemistry and life science and material science. Not only some constituent substances in the human body and other living beings have heterocyclic structures, such as amino acids, nucleic acids, etc., but also the heterocyclic compounds used as medicines are numerous. In addition, it also has a wide range of applications in industries such as pesticides and plastics. [0003] Pyrrolone compounds play an important role in the structure of the ring framework of tetrahydropyrrole compounds such as porphine, porphyrin and corrin. In addition, pyrrolidone has many uses in the fields of medicine, food, daily chemicals, coatings, and polymer polymerization. Oxygen...

Claims

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Application Information

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IPC IPC(8): C07D498/04
Inventor 郝健侯明华庄红伟万文蒋海珍
Owner SHANGHAI UNIV
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