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N-[(3,4,5-trifluoro)phenyl]acrylamide and preparation method thereof

A technology of acrylamide and trifluoroaniline, which is applied in the preparation of carboxylic acid amide, chemical instruments and methods, and the preparation of organic compounds, etc., can solve the problems of great harm to the human body and the environment, non-compliance with environmental protection, and high catalyst toxicity. The effect of less industrial waste, low price and low raw material price

Active Publication Date: 2019-10-25
YELLOW RIVER CONSERVANCY TECHN INST
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  • Summary
  • 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 preparation method thereof
  • N-[(3,4,5-trifluoro)phenyl]acrylamide and preparation method thereof
  • N-[(3,4,5-trifluoro)phenyl]acrylamide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0037] Add 14.7 grams (0.1mol) of 3,4,5-trifluoroaniline and 50 grams of reaction solvent (the reaction solvent is dimethylformamide) into a 500ml four-necked bottle, add sodium bicarbonate, sodium bicarbonate and 3,4 , The mass ratio of 5-trifluoroaniline is 0.01:1, stir and cool down to 5°C, add 22.6 grams (0.25 moles) of acryloyl chloride dropwise, after the dropwise addition, react at 5°C for 5 hours, and cool the reaction solution to room temperature , and then add 300ml 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 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 Catalyst dosage discussion experiment

[0041]

[0042] As can be seen from Table 1, 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, Only 35.3%, this is because catalyst consumption is few, and reaction activity is low, causes product yield to be low. Along with the increase of sodium bicarbonate and 3,4,5-trifluoroaniline mass ratio, the yield of N-[(3,4,5-trifluoro)phenyl]acrylamide improves gradually, when sodium bicarbonate and When 3,4,5-trifluoroaniline mass ratio was 0.05:1, the product yield had reached 74.2%, and further increasing the consumption of sodium bicarbonate had little impact on the product yield, therefore, sodium bicarbonate and 3 , The mass ratio o...

Embodiment 7

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

[0047] Add 14.7 grams (0.1mol) of 3,4,5-trifluoroaniline and 50 grams of reaction solvent (the reaction solvent is dimethylformamide) into a 500ml four-necked bottle, 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 to acryloyl chloride is 1:1, dropwise After completion, react at 5°C for 5 hours, lower the reaction solution to room temperature, then add 300ml 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 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 particularly relates to N-[(3,4,5-trifluoro)phenyl]acrylamide and a preparation method thereof. The preparation method of the N-[(3,4,5-trifluoro)phenyl]acrylamide comprises the following specific steps: (1) 3,4,5-trifluorobenzenamine, a reaction solvent and a catalyst are added into a reaction container, stirred and evenly mixed, and then acryloyl chloride is added to react for 1-7 h at minus10-30 DEG C; and (2) water is added into reaction liquid obtained in the step (1) and evenly stirred, filtering is conducted, sediment is separated and dried, and then the N-[(3,4,5-trifluoro)phenyl]acrylamide is obtained. According to the preparation method, the raw materials are simple and easy to obtain, the cost is low, operation is easy, and the N-[(3,4,5-trifluoro)phenyl]acrylamide is high in yield and purity; and a reaction amplification process is simple and feasible through a weak alkaline catalyst, namely sodium bicarbonate, three waste generated by a reaction is less, and thus environmental protection is achieved.

Description

technical field [0001] 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. Background technique [0002] Fluorine is the most electronegative element, the atomic covalent radius (0.064nm) is very small, the C-F bond energy is very 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 are widely used in the treatment of cancer, atherosclerosis, restenosis, endometriosis and psoriasis and other diseases. In the field of macromolecules, polymers containing fluorinated acrylamide monom...

Claims

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Application Information

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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