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5-trifluoromethyl-4H-imidazoline-4-ketone derivative and synthetic method

The technology of a trifluoromethyl group and a synthesis method is applied in the field of 5-trifluoromethyl-4H-imidazolin-4-one derivatives and synthesis, and can solve problems such as blanks, achieve simple operation, high product yield, The effect of wide substrate adaptability

Active Publication Date: 2018-12-11
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • 5-trifluoromethyl-4H-imidazoline-4-ketone derivative and synthetic method

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Effect test

Embodiment 1

[0033] A kind of synthetic method of 5-trifluoromethyl-4H-imidazolin-4-ketone derivative, comprises the following steps:

[0034] Under air atmosphere, in a 25 ml reaction flask equipped with a reflux condenser, add 0.2 mmol of benzamidine hydrochloride, 0.5 mmol of potassium tert-butoxide, 0.4 mmol of 3-phenyl-1,1,1 ,-trifluoroacetone, 2 ml N,N-dimethylformamide, the reaction system was stirred at 70°C for 12 hours, stopped heating and stirring, cooled to room temperature, added water, extracted the reaction solution with ethyl acetate, and distilled ethyl acetate The ester layer was rotary evaporated 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 mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 10:1; The yield was 96%.

Embodiment 2

[0036] A kind of synthetic method of 5-trifluoromethyl-4H-imidazolin-4-ketone derivative, comprises the following steps:

[0037] Under air atmosphere, in a 25 ml reaction flask equipped with a reflux condenser, add 0.2 mmol of benzamidine hydrochloride, 0.8 mmol of potassium carbonate, 0.4 mmol of 3-phenyl-1,1,1,- Trifluoroacetone, 2 ml of N,N-dimethylformamide, the reaction system was stirred at 70°C for 12 hours, stopped heating and stirring, cooled to room temperature, added water, extracted the reaction solution with ethyl acetate, and extracted the ethyl acetate layer Carry out decompression rotary evaporation to remove solvent, then separate and purify by column chromatography to obtain the target product, the used column chromatography eluent is petroleum ether: ethyl acetate mixed solvent with a volume ratio of 10:1; the yield of the product is 65%.

Embodiment 3

[0039] A kind of synthetic method of 5-trifluoromethyl-4H-imidazolin-4-ketone derivative, comprises the following steps:

[0040] Under air atmosphere, in a 25 ml reaction flask equipped with a reflux condenser, add 0.2 mmol of benzamidine hydrochloride, 0.2 mmol of potassium tert-butoxide, 0.4 mmol of 3-phenyl-1,1,1 ,-trifluoroacetone, 2 ml 1,4-dioxane, the reaction system was stirred at 70°C for 12 hours, stopped heating and stirring, cooled to room temperature, added water, extracted the reaction solution with ethyl acetate, and distilled ethyl acetate The layer is subjected to decompression rotary evaporation to remove the solvent, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used is a volume ratio of 10:1 petroleum ether: ethyl acetate mixed solvent; the yield of the product 10%.

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Abstract

The invention belongs to the technical field of medicine chemical synthesis, and discloses a 5-trifluoromethyl-4H-imidazoline-4-ketone derivative as well as a synthetic method. The synthetic method comprises the following steps: in an alkali and an organic solvent, enabling an amidine salt to react with trifluoromethyl ketone compound, and performing the subsequent treatment, thus obtaining the 5-trifluoromethyl-4H-imidazoline-4-ketone derivative. The structure of the 5-trifluoromethyl-4H-imidazoline-4-ketone derivative is as shown in formula I. By adopting the method of the invention, the useof a transitional metal catalyst can be avoided, and the used raw material is nontoxic, cheap and easy to obtain; and the reaction is good in adaptability to functional groups, wide in adaptability to the substrate, high in product yield, capable of realizing the mass production in a gram scale, and favorable for the industrial production, and the prepared product has wide use in the fields suchas pesticides, medicine, materials and the like. (Shown in the description).

Description

technical field [0001] The invention belongs to the technical field of materials, pharmaceutical and chemical synthesis, and specifically relates to a 5-trifluoromethyl-4H-imidazolin-4-one derivative and a synthesis method. Background technique [0002] In view of the small atomic radius and high electronegativity of fluorine atoms, it is difficult to be polarized. Therefore, the introduction of fluorine atoms or fluorine-containing groups into organic compound molecules usually significantly improves the chemical properties, physical properties and biological activities of the compounds. 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 fluorine-containing natural products existing in nature are very limited. In order to meet the urgent needs of people's production and research on the increase in the number and types of organic fluorinated comp...

Claims

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Application Information

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Patent Type & Authority Applications(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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