n-[(3,4,5-trifluoro)phenyl]acrylamide and its preparation method

A technology of acrylamide and trifluoroaniline, which is applied in the preparation of carboxylic acid amides, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of great harm to the human body and the environment, not conforming to green environmental protection, and high toxicity of catalysts. The effect of less industrial waste, low price and low raw material price

Active Publication Date: 2022-05-24
YELLOW RIVER CONSERVANCY TECHN INST
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the existing methods for synthesizing fluorinated acrylamide monomers have high catalyst toxicity, great harm to the human body and the environment, and do not meet the requirements of today's green environmental protection. Moreover, additional polymerization inhibitors need to be added during the reaction process, and the reaction cost is high.

Method used

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  • n-[(3,4,5-trifluoro)phenyl]acrylamide and its preparation method
  • n-[(3,4,5-trifluoro)phenyl]acrylamide and its preparation method
  • n-[(3,4,5-trifluoro)phenyl]acrylamide and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A preparation method of N-[(3,4,5-trifluoro)phenyl]acrylamide, the specific steps are as follows:

[0037] Add 14.7 grams (0.1 mol) of 3,4,5-trifluoroaniline and 50 grams of reaction solvent (the reaction solvent is dimethylformamide) into a 500ml four-necked flask, add sodium bicarbonate, sodium bicarbonate and 3,4 , The mass ratio of 5-trifluoroaniline is 0.01:1, the temperature is lowered to 5 ° C with stirring, 22.6 g (0.25 mol) of acryloyl chloride is added dropwise, after the dropwise addition, the reaction is carried out at 5 ° C for 5 hours, and the reaction solution is lowered to room temperature , and then add 300 ml of deionized water to the reaction solution, filter, collect the precipitate, and dry the precipitate to obtain N-[(3,4,5-trifluoro)phenyl]acrylamide. The purity of the prepared N-[(3,4,5-trifluoro)phenyl]acrylamide was determined by high performance liquid chromatography.

Embodiment 2～ Embodiment 6

[0039] The contents of Examples 2 to 6 are basically the same as those of Example 1, except that the mass ratio of sodium bicarbonate to 3,4,5-trifluoroaniline is different, see Table 1 for details.

[0040] Table 1 Experiments to explore the amount of catalyst

[0041]

[0042] It can be seen from Table 1 that when the mass ratio of sodium bicarbonate and 3,4,5-trifluoroaniline is 0.01:1, the yield of N-[(3,4,5-trifluoro)phenyl]acrylamide is low, It is only 35.3%, which is due to the low amount of catalyst and low reaction activity, resulting in low product yield. With the increase of the mass ratio of sodium bicarbonate to 3,4,5-trifluoroaniline, the yield of N-[(3,4,5-trifluoro)phenyl]acrylamide gradually increased. When the mass ratio of 3,4,5-trifluoroaniline is 0.05:1, the product yield reaches 74.2%, and further increasing the amount of sodium bicarbonate has little effect on the product yield. Therefore, sodium bicarbonate and 3 , The mass ratio of 4,5-trifluoroan...

Embodiment 7

[0046] A preparation method of N-[(3,4,5-trifluoro)phenyl]acrylamide, the specific steps are as follows:

[0047] Add 14.7 grams (0.1 mol) of 3,4,5-trifluoroaniline and 50 grams of reaction solvent (the reaction solvent is dimethylformamide) into a 500ml four-necked flask, add 0.735 grams of sodium bicarbonate, sodium bicarbonate and 3 , The mass ratio of 4,5-trifluoroaniline is 0.05:1, the temperature is lowered to 5 °C with stirring, and acryloyl chloride is added dropwise. The molar ratio of 3,4,5-trifluoroaniline and acryloyl chloride is 1:1, and the After completion, the reaction was carried out at 5 °C for 5 hours, the reaction solution was lowered to room temperature, 300 ml of deionized water was added to the reaction solution, filtered, and the precipitate was collected. The precipitate was dried to obtain N-[(3,4,5- trifluoro)phenyl]acrylamide. The purity of the prepared N-[(3,4,5-trifluoro)phenyl]acrylamide was determined by high performance liquid chromatography. ...

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Abstract

The invention belongs to the technical field of organic synthesis, and specifically relates to N-[(3,4,5-trifluoro)phenyl]acrylamide and a preparation method thereof. The specific steps of the preparation method of N-[(3,4,5-trifluoro)phenyl]acrylamide are as follows: (1) 3,4,5-trifluoroaniline, reaction solvent and catalyst are added to the reaction vessel, stirred and mixed Then add acryloyl chloride and react at -10°C to 30°C for 1 to 7 hours; (2) Add water to the reaction solution obtained in step (1), stir and mix, filter, separate the precipitate, and dry the precipitate , to obtain N‑[(3,4,5‑trifluoro)phenyl]acrylamide. The preparation method of the present invention has simple and easy-to-obtain raw materials, low cost, simple operation, high yield and high purity of N-[(3,4,5-trifluoro)phenyl]acrylamide; weakly basic catalyst—sodium bicarbonate The reaction amplification process is simple and feasible, the three wastes produced by the reaction are less, and the reaction is green and environmentally friendly.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a N-[(3,4,5-trifluoro)phenyl]acrylamide and a preparation method thereof. Background technique [0002] Fluorine is the most electronegative element, the atomic covalent radius (0.064nm) is very small, the C-F bond energy is large (485KJ / mol), and the arrangement of fluorine atoms in the outer layer of the carbon skeleton is very tight, which can affect the main chain and Internal molecules form a "shielding effect", and fluorinated acrylamide monomers have unique functions due to the presence of fluorine groups. Fluorinated acrylamide monomers are not only used as fungicides to prevent crop diseases and insect pests, but also as tyrosine kinase inhibitors. They are widely used in the treatment of cancer, atherosclerosis, restenosis, endometriosis and psoriasis. and other diseases. In the field of polymers, polymers containing fluorinated acrylamide monomer structures...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/02C07C233/15C08F20/54
CPCC07C231/02C07C233/15C08F20/54
Inventor 姚新鼎方瑞娜庞宏建刘伟马金菊崔鹏冯涛
Owner YELLOW RIVER CONSERVANCY TECHN INST
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