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A kind of 5-trifluoromethyl-4h-imidazolin-4-one derivative and its synthesis method

A technology of trifluoromethyl ketone and trifluoromethyl, which is applied in the field of 5-trifluoromethyl-4H-imidazolidin-4-one derivatives and synthesis, can solve problems such as blanks, and achieve simple operation and good industrial Application prospect and wide substrate adaptability

Active Publication Date: 2022-04-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, 5-trifluoromethyl-4H-imidazolin-4-one derivatives and their synthetic methods have not been reported, and the research on such compounds and their synthetic techniques is still blank.
Therefore, the development of efficient methods for the synthesis of 5-trifluoromethyl-4H-imidazolin-4-one compounds is still a challenging research topic

Method used

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  • A kind of 5-trifluoromethyl-4h-imidazolin-4-one derivative and its synthesis method
  • A kind of 5-trifluoromethyl-4h-imidazolin-4-one derivative and its synthesis method
  • A kind of 5-trifluoromethyl-4h-imidazolin-4-one derivative and its synthesis method

Examples

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Effect test

Embodiment 1

[0033] Synthesis method of 5-(trifluoromethyl)-4H-imidazoline-4-one derivative, comprising the following steps:

[0034]In an air atmosphere, in a 25 ml reaction bottle equipped with a reflux condensing tube, 0.2 mmol benzamidine hydrochloride, 0.5 mmol potassium tert-butanol, 0.4 mmol 3-phenyl-1,1,1,-trifluoroacetone, 2 ml N, N-dimethylformamide, the reaction system stirred the reaction at 70 °C for 12 hours, stopped heating and stirring, cooled to room temperature, added water, ethyl acetate extraction reaction liquid, the ethyl acetate layer was steamed under reduced pressure, the solvent was removed, and then separated and purified by column chromatography. To obtain the target product, the column chromatography eluent used was a petroleum ether: ethyl acetate mixed solvent with a volume ratio of 10:1; the yield of the product was 96%.

Embodiment 2

[0036] Synthesis method of 5-(trifluoromethyl)-4H-imidazoline-4-one derivative, comprising the following steps:

[0037] In an air atmosphere, in a 25 ml reaction bottle equipped with a reflux condensing tube, 0.2 mmol benzamidine hydrochloride, 0.8 mmol potassium carbonate, 0.4 mmol 3-phenyl-1,1,1,-trifluoroacetone, 2 ml N, N-dimethylformamide, the reaction system stirred the reaction at 70 °C for 12 hours, stopped heating and stirring, cooled to room temperature, added water, ethyl acetate extraction reaction solution, the ethyl acetate layer was distilled under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product The column chromatography eluent used was a petroleum ether:ethyl acetate mixed solvent with a volume ratio of 10:1; the yield of the product was 65%.

Embodiment 3

[0039] Synthesis method of 5-(trifluoromethyl)-4H-imidazoline-4-one derivative, comprising the following steps:

[0040] In an air atmosphere, in a 25 ml reaction bottle equipped with a reflux condensing tube, 0.2 mmol benzamidine hydrochloride, 0.2 mmol potassium tert-butanol, 0.4 mmol 3-phenyl-1,1,1,-trifluoroacetone, 2 ml 1,4-dioxane, the reaction system stirred the reaction at 70 °C for 12 hours, stopped heating and stirring, cooled to room temperature, added water, ethyl acetate extraction reaction liquid, the ethyl acetate layer was hydrobolic to remove the solvent by pressure rotation, and then separated and purified by column chromatography to obtain the target product, The column chromatography eluent used was a petroleum ether:ethyl acetate mixed solvent with a volume ratio of 10:1; the yield of the product was 10%.

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Abstract

The invention belongs to the technical field of pharmaceutical chemical synthesis, and discloses a 5-trifluoromethyl-4H-imidazolin-4-one derivative and a synthesis method. The synthesis method: in an alkali and an organic solvent, react an amidine salt with a trifluoromethyl ketone compound, and perform subsequent treatment to obtain a 5-trifluoromethyl-4H-imidazolin-4-one derivative. The structure of the 5-trifluoromethyl-4H-imidazolin-4-one derivative of the present invention is formula I. The method of the invention avoids the use of transition metal catalysts, and the raw materials used are non-toxic, cheap and easy to obtain; the reaction has good adaptability to functional groups, wide adaptability to substrates, high product yield, can be enlarged to gram-scale production and synthesis, and is beneficial to industrial production , the obtained product has wide application in the field of pesticide, medicine and material.

Description

Technical field [0001] The present invention belongs to the field of materials, pharmaceutical and chemical synthesis technology, specifically relates to a 5-trifluoromethyl-4H- imidazoline-4-one derivative and synthesis method. Background [0002] Given the small atomic radius of the fluorine atom and its high electronegativity, it is difficult to be polarized. Thus, the introduction of fluorine atoms or fluorine-containing groups into organic compound molecules typically significantly improves the chemical, physical, and biological activity of the compound. According to statistics, more than 30% of the pesticide or drug molecules sold on the market contain at least one fluorine atom or fluorine-containing group. However, the types of fluorinated natural products that exist in nature are very limited. In order to meet the urgent need for people to produce and study the increase in the number and variety of organic fluorine-containing compounds, the development of methods for th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/70C07D401/04
CPCC07D233/70C07D401/04
Inventor 竺传乐江焕峰
Owner SOUTH CHINA UNIV OF TECH
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