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A kind of trifluoroacetyl substituted hydrazone derivative and its synthesis method

A technology of trifluoroacetyl group and synthesis method, which is applied in the field of trifluoroacetyl group substituted hydrazone derivatives and the synthesis field thereof, can solve problems such as blank, and achieve the effects of simple operation, mild reaction conditions and high product yield

Active Publication Date: 2021-08-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, simple N-aryl-trifluoroacetyl substituted hydrazone compounds and their synthesis methods have not been reported, and the research on such compounds and their synthesis technology is still blank.
Therefore, the development of efficient synthetic methods for the synthesis of N-aryl-trifluoroacetyl substituted hydrazones is still a challenging research topic.

Method used

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  • A kind of trifluoroacetyl substituted hydrazone derivative and its synthesis method
  • A kind of trifluoroacetyl substituted hydrazone derivative and its synthesis method
  • A kind of trifluoroacetyl substituted hydrazone derivative and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In a 25ml reaction flask, add 0.2mmol of p-methoxyphenyldiazonium tetrafluoroborate, 0.3mmol of triethylenediamine, 0.3mmol of 3-phenyl-1,1,1,-trifluoro Acetone, 2 ml of acetonitrile, and the reaction system was stirred at 25°C for 0.05 hour. Add water, extract the reaction solution with ethyl acetate, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent used is petroleum ether: ethyl acetate with a volume ratio of 10:1 ester mixed solvent to obtain the product with a yield of 97%.

Embodiment 2

[0031] In a 25ml reaction flask, add 0.2mmol of p-methoxyphenyldiazonium tetrafluoroborate, 0.3mmol of triethylenediamine, 0.3mmol of 3-phenyl-1,1,1,-trifluoro Acetone, 2 ml of acetonitrile, and the reaction system was stirred at 25°C for 0.05 hour. Add water, extract the reaction solution with methylene chloride, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent used is petroleum ether:ethyl acetate in a volume ratio of 10:1 ester mixed solvent to obtain the product with a yield of 97%.

Embodiment 3

[0033] In a 25 ml reaction flask, add 0.2 mmol p-methoxyphenyldiazonium hexafluorophosphate, 0.3 mmol potassium carbonate, 0.3 mmol 3-phenyl-1,1,1,-trifluoroacetone, 2 mL of acetonitrile, and the reaction system was stirred at 25°C for 0.05 hour. Add water, extract the reaction solution with ethyl acetate, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent used is petroleum ether: ethyl acetate with a volume ratio of 10:1 ester mixed solvent to obtain the product with a yield of 64%.

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a trifluoroacetyl-substituted hydrazone derivative and a synthesis method thereof. The trifluoroacetyl substituted hydrazone derivative has the structural formula shown in formula (I), and its synthesis method is: in the reactor, add diazonium salt, trifluoromethyl ketone, alkali and solvent, Stir the reaction at ℃ for 0.05-24 hours, cool to room temperature after the reaction, add water, extract the reaction solution with an organic solvent, evaporate the solvent to obtain a crude product, and purify by column chromatography to obtain a trifluoroacetyl-substituted hydrazone derivative. The synthetic method of the present invention does not use a catalyst, does not need ligands, 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, and high product yield; and the operation is simple and safe, and the reaction conditions Mild, with good industrial application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a trifluoroacetyl-substituted hydrazone derivative and a synthesis method thereof. 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 compounds, the development ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/86C07C249/16C07C317/34C07C315/04C07D215/38
CPCC07C249/16C07C251/86C07C315/04C07C317/34C07D215/38
Inventor 竺传乐江焕峰
Owner SOUTH CHINA UNIV OF TECH