Mechanochemical preparation of 1,3,5-triaryl-2-pyrazoline compounds

A mechanochemical and compound technology, applied in 1 field, to achieve the effects of high reaction yield, low production cost and high yield

Inactive Publication Date: 2009-05-27
ZHEJIANG UNIV OF TECH
View PDF0 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In recent years, some people also use K 2 CO 3 or SiO 2 etc. are used as catalysts to prepare pyrazoline compounds under ultrasonic or microwave conditions, but these methods are still in the re...

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Mechanochemical preparation of 1,3,5-triaryl-2-pyrazoline compounds
  • Mechanochemical preparation of 1,3,5-triaryl-2-pyrazoline compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of 1,3,5-triphenyl-2-pyrazoline

[0023] Add chalcone (2.08g, 10mmol), phenylhydrazine (1.08g, 10mmol), potassium hydrogen sulfate (0.14g, 1mmol) and silica gel (10g) into a 75mL ball milling jar, then add the milling ball and tighten the lid. Put the ball mill jar into the ball mill and run at 1290 rpm to make the mixture react for 5 min, TLC (sample dissolved in ethyl acetate) to track the progress of the reaction. After the reaction, the reaction mixture was washed with hot absolute ethanol, filtered, and the filtrate was boiled to evaporate part of the ethanol to saturation, cooled to room temperature, precipitated a solid, and dried to obtain 1,3,5-triphenyl- 2.72 g of 2-pyrazoline, the yield was 91%.

[0024] White solid, Mp: 134°C. IR (KBr): 3129, 1490, 1400cm -1 . 1 H NMR(400MHz, DMSO-d 6 ): δ(ppm)=7.76-6.71(m, 15H, ArH), 5.48(dd, J=5.2, 9.6Hz1H, ArCHN), 3.93(dd, J=9.6, 14.0Hz1H, CH 2 C=N), 3.11(dd, J=5.2, 14.0Hz1H, CH 2 C=N). 13 C NMR (100MHz...

Embodiment 2

[0025] Example 2: Preparation of 1,3,5-triphenyl-2-pyrazoline

[0026] Add chalcone (2.08g, 10mmol), phenylhydrazine (2.16g, 20mmol), potassium hydrogen sulfate (0.07g, 0.5mmol) and silica gel (10g) into a 75mL ball milling jar, then add the milling ball and tighten the lid. Put the ball mill jar into the ball mill and run at 1290 rpm to make the mixture react for 5 min, TLC (sample dissolved in ethyl acetate) to track the progress of the reaction. The separation and purification steps were the same as in Example 1, to obtain 2.77 g of 1,3,5-triphenyl-2-pyrazoline, with a yield of 93%, and the physical data were the same as in Example 1.

Embodiment 3

[0027] Example 3: Preparation of 1,3,5-triphenyl-2-pyrazoline

[0028] Add chalcone (2.08g, 10mmol), phenylhydrazine (5.41g, 50mmol), potassium hydrogen sulfate (0.27g, 2mmol) and silica gel (21g) into a 75mL ball milling jar, then add the milling ball and tighten the lid. Put the ball mill jar into the ball mill and run at 1290 rpm to make the mixture react for 5 min, TLC (sample dissolved in ethyl acetate) to track the progress of the reaction. The separation and purification steps were the same as in Example 1, to obtain 2.69 g of 1,3,5-triphenyl-2-pyrazoline, with a yield of 90%, and the physical data were the same as in Example 1.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a mechanochemical preparation method for a 1, 3, 5-triaryl-2-pyrazoline compound with a structure shown in a formula (III). The method comprises the following steps: a chalcone compound with a structure shown in a formula (I) and a phenyl hydrazine compound with a structure shown in a formula (II) are taken as raw materials, hydrosulfate is taken as a catalyst, and silica gel is taken as a grinding aid to perform a ball milling reaction in a closed ball milling tank; and after the reaction is finished, a reaction mixture is separated and purified to obtain the 1, 3, 5-triaryl-2-pyrazoline compound with the structure shown in the formula (III). The method has the advantages of safe and reliable production, simple and convenient operation, short reaction time, generally higher reaction yield, low production cost, simple post-treatment, small pollution and so on, and is the preparation method for the 1, 3, 5-triaryl-2-pyrazoline compound with better popularization and application prospects.

Description

(1) Technical field [0001] The invention relates to a mechanochemical preparation method of 1,3,5-triaryl-2-pyrazoline compounds. (2) Background technology [0002] Pyrazoline compounds have broad prospects as medicines. Such compounds have obvious anti-inflammatory, analgesic, antibacterial, bactericidal, insecticidal and other activities. In addition, some polysubstituted pyrazoline compounds have good optical properties and can be used as fluorescent switches, polishing agents and molecular probes. Among the many pyrazoline compounds, 1,3,5-triaryl-2-pyrazoline is the most studied compound, and its biological activity and preparation methods are generally valued by chemists. [0003] The research on the preparation of 1,3,5-triaryl-2-pyrazoline compounds has a long history. The classic method is to obtain the target product by reacting chalcone compounds with phenylhydrazine compounds. This method mostly uses AcOH, HCl, Et in a solvent 3 N, Ba(OH) 2 Or NaOH and other strong ac...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D231/06
Inventor 李振华朱兴一苏为科郭巧凤吴倩倩徐丽
Owner ZHEJIANG UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap