Preparation method of pyrazolone derivative

A pyrazolone and derivative technology, applied in the field of heterocyclic compounds in organic chemistry, can solve the problems of not promoting the best conversion of raw materials, not very environmentally friendly, increasing energy consumption, etc., and achieving excellent yield and reaction time. Short, safe effect

Inactive Publication Date: 2019-08-16
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] First of all, the provided method needs to be heated to 90°C to react. The reaction at high temperature requires a lot of energy. From the perspective of energy saving and environmental protection, although green water is used as a solvent, energy consumption is inevitable.
[0011] Secondly, the reaction time is long, the duration is 6-8 hours, and the efficiency of the reaction is relatively low
[0012] Third, the yield of 4,4'-(arylmethylene)bis(1-aryl-3-trifluoromethyl-1H-pyrazol-5(4H)-one) compound prepared by the provided method was 70 % ~ 89%, not the most ideal conversion rate, did not promote the best conversion of raw materials
[0018] Third, the method provided requires the use of petroleum ether and ethyl acetate as reaction solvents, which does not meet the requirements of environmental protection
Fourth, although the reaction time is shortened, the reaction process requires a second heating-cooling process, which increases energy consumption

Method used

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  • Preparation method of pyrazolone derivative
  • Preparation method of pyrazolone derivative
  • Preparation method of pyrazolone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: 1-phenyl-3-trifluoromethyl-5-pyrazolone (456.0mg, 2.0mmol) and benzaldehyde (106.2mg, 1.0mmol) were added to a 25mL round bottom flask, and 5mL ethyl acetate Dissolve the ester, add 7g of crude silica gel, mix well and spin dry with a rotary evaporator. Put a magnet and stir at room temperature under the action of a magnetic stirrer for 12 minutes, take a small amount of the mixture and dissolve it in a solvent, track it on a TLC plate, after the reaction is completed, wash the mixture with an appropriate amount of ethyl acetate, filter to remove the crude silica gel, and remove the filtrate under reduced pressure The solvent was used to obtain the crude product, and the crude product was purified by ethanol recrystallization to obtain the pure product compound 4,4'-(aryl methylene)bis(1-aryl-3-trifluoromethyl-1H-pyrazole-5(4H) -ketone) (490.0 mg, 90%).

[0031] The structure of this compound is:

[0032]

[0033] Molecular formula: C 27 h 19 f 6 N 4...

Embodiment 2

[0044] Example 2: Add 1-phenyl-3-trifluoromethyl-5-pyrazolone (456.0mg, 2.0mmol), 4-nitrobenzaldehyde (152.2mg, 1.0mmol) into a 25mL round bottom flask, Dissolve in 5 mL of ethyl acetate, add 5 g of crude silica gel, mix well and spin dry with a rotary evaporator. Put magnets into the mixture obtained by spin-drying the solvent, stir at room temperature under the action of a magnetic stirrer for 10 minutes, take a small amount of the mixture and dissolve it in a solvent, track it on a TLC plate, after the reaction is completed, wash the mixture with an appropriate amount of ethyl acetate, and filter The crude silica gel was removed, and the filtrate was decompressed to remove the solvent to obtain the crude product, which was purified by ethanol recrystallization to obtain the pure product compound 4,4'-(4-nitrobenzylidene)bis(1-phenyl-3-tri Fluoromethyl-1H-pyrazol-5(4H)-one) (552.4 mg, 97%).

[0045] The structure of this compound is:

[0046]

[0047] Molecular formula:...

Embodiment 3

[0058] Example 3: Add 1-phenyl-3-trifluoromethyl-5-pyrazolone (456.0mg, 2.0mmol), 4-methoxybenzaldehyde (163.4mg, 1.2mmol) in a 25ml round bottom flask , dissolved in 5 mL of ethyl acetate, added 10 g of crude silica gel, mixed evenly, and spin-dried the solvent with a rotary evaporator. Put the magneton into the mixture obtained by spin-drying the solvent, stir at room temperature with a magnetic stirrer for 15 minutes, take a small amount of the mixture and dissolve it in a solvent, and track it on a TLC plate. After the reaction is completed, wash the mixture with an appropriate amount of ethyl acetate and filter it out. Crude silica gel, the filtrate was decompressed to remove the solvent to obtain the crude product, the crude product was purified by ethanol recrystallization to obtain the pure product compound 4,4'-(4-p-methoxybenzylidene)bis(1-phenyl-3- Trifluoromethyl-1H-pyrazol-5(4H)-one) (506.8 mg, 89%).

[0059] The structure of this compound is:

[0060]

[006...

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Abstract

The present invention relates to a preparation method of a pyrazolone derivative. The method comprises the following steps: 1-substituted-3-trifluoromethyl-5-pyrazolone, substituted benzaldehyde and an appropriate amount of an additive reagent-grade crude silica gel are uniformly mixed, and then are stirred at room temperature to a obtain compound 4,4'-(arylmethylene)bis(1-aryl-3-trifluoromethyl-1H-pyrazole-5(4H)one), and the solid crude silica gel which is filtered out is washed with an appropriate amount of a solvent, and is dried for cycle use. The method of the invention has the advantagesof environment friendliness, easily available raw materials, mild reaction conditions, simplicity in experiment operation, strong universality, convenience in post-treatment of the product, cycle useof the additive crude silica gel after simple treatment, and high yield of the product.

Description

technical field [0001] The invention belongs to the field of heterocyclic compounds in organic chemistry, and relates to a preparation method of pyrazolone derivatives. Especially a kind of preparation method of 4,4'-(aryl methylene)bis(1-aryl-3-trifluoromethyl-1H-pyrazol-5(4H)-one) Background technique [0002] Nowadays, pyrazolone derivatives have attracted more and more attention and research due to various other drugs and biological activities. Pyrazolone compounds can be used as anticancer antibiotics, cytokine inhibitors, biological enzyme inhibitors and so on. The compound containing two pyrazolone heterocycles has antibacterial, antiviral, anti-inflammatory and antidepressant activities, and it can also be used as an extraction agent or a ligand for certain metal ions. Currently [0003] Document 1: The reported synthesis method of 4,4'-(arylmethylene)bis(1-aryl-3-trifluoromethyl-1H-pyrazol-5(4H)-one), as shown in Scheme 1 Shown: 1-aryl-3-trifluoromethyl-5-pyrazo...

Claims

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Application Information

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IPC IPC(8): C07D231/22
CPCC07D231/22
Inventor 宋力平陈帆辉李泽钰段雯雯张敏
Owner SHANGHAI UNIV
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