Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

3-[4-(2-amino-5-substituted-[1,3,4]thiadiazolyl)-phenyl]-1-ferrocenyl-acrylketone and preparation method thereof

A ferrocene-based, propylene ketone technology, applied in chemical instruments and methods, metallocene, sustainable manufacturing/processing, etc., to achieve the effects of easy automatic control, uniform heating temperature, and complete reaction

Inactive Publication Date: 2014-09-24
SHAANXI UNIV OF SCI & TECH
View PDF4 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many reports on the synthesis and application of ferrocene derivatives and 1,3,4-thiadiazole compounds, but there are few reports on the introduction of ferrocene groups into 1,3,4-thiadiazole compounds

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
  • 3-[4-(2-amino-5-substituted-[1,3,4]thiadiazolyl)-phenyl]-1-ferrocenyl-acrylketone and preparation method thereof
  • 3-[4-(2-amino-5-substituted-[1,3,4]thiadiazolyl)-phenyl]-1-ferrocenyl-acrylketone and preparation method thereof
  • 3-[4-(2-amino-5-substituted-[1,3,4]thiadiazolyl)-phenyl]-1-ferrocenyl-acrylketone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 10 mmol of acetylferrocene, 11 mmol of 4-(2-amino-[1,3,4]thiadiazole)-benzaldehyde (R is -H), 1 mmol of NaOH and 20 mL of absolute ethanol to a reflux condenser In a three-necked flask, place the flask in a microwave oven, and perform multiple microwave radiations at a power of 140W, each time for 1min, and the interval between two radiations is 15s, until the reaction is complete, and the reaction process is monitored by TLC. When the raw material point of ferrocene disappears, it means that the reaction is complete, and the developer used by TLC is a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:3; after the reaction, the reaction product is filtered, and the filtrate is extracted with acetone. The organic matter, the filter residue is recovered and reused, and then the acetone in the extract is removed by rotary evaporation, and then separated by silica gel column chromatography, and the mixed solution of petroleum ether and ethyl acetate w...

Embodiment 2

[0035] 10mmol acetyl ferrocene, 12mmol 4-(2-amino-5-methyl-[1,3,4]thiadiazole)-benzaldehyde (R is methyl), 1mmol KF / Al 2 o 3 and 25mL of absolute ethanol were added to a three-necked flask with a reflux condenser, the flask was placed in a microwave oven, and microwave radiation was performed several times at a power of 150W, each time for 1.5min, and the interval between two radiations was 15s until The reaction is complete, and the reaction process is monitored by TLC. When it is found that the raw material point of acetylferrocene disappears, it means that the reaction is complete, and the developing agent used by TLC is a mixed solution of ethyl acetate and sherwood oil with a volume ratio of 1:3; After the reaction, the reaction product was filtered, the filtrate was extracted with acetone to extract the organic matter, the filter residue was recovered and reused, and then the acetone in the extract was removed by rotary evaporation, and then separated by silica gel colum...

Embodiment 3

[0039] Add 10mmol acetylferrocene, 11mmol 4-(2-amino-5-ethyl-[1,3,4]thiadiazole)-benzaldehyde (R is ethyl), 0.5mmol NaOH and 10mL absolute ethanol Put the flask into a three-necked flask with a reflux condenser, place the flask in a microwave oven, and perform multiple microwave radiations at a power of 145W, each time for 2min, and the interval between two radiations is 25s, until the reaction is complete, and the reaction process is analyzed by TLC. Carry out monitoring, when finding that the raw material point of acetyl ferrocene disappears, it means that the reaction is complete, wherein the developer used by TLC is a mixed solution of ethyl acetate and sherwood oil with a volume ratio of 1:3; after the reaction, the reaction product is filtered , the filtrate is extracted with acetone to extract the organic matter, the filter residue is recovered and reused, and then the acetone in the extract is removed by rotary evaporation, and then separated by silica gel column chroma...

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 provides a 3-[4-(2-amino-5-substituted-[1,3,4]thiadiazolyl)-phenyl]-1-ferrocenyl-acrylketone and a preparation method thereof. The structural formula is disclosed in the specification. The preparation method comprises the following steps: adding acetylferrocene, 4-(2-amino-5-substituted-[1,3,4]thiadiazolyl)-benzaldehyde, catalyst and anhydrous ethanol into a flask with a reflux condensation tube, putting the flask into microwave oven, carrying out microwave radiation until the reaction is completed, extracting the reaction product with acetone, and removing the acetone to obtain the target product. The method for synthesizing the target product by the microwave process has the advantages of high reaction sensitivity, high heating rate, short reaction time, high heat utilization efficiency, energy saving, no pollution and the like; and the obtained product has the advantages of high purity and high yield (up to 91% above).

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a 3-[4-(2-amino-5-substituted-[1,3,4]thiadiazole)-phenyl]-1-ferrocenyl-propenone and its preparation method. Background technique [0002] Ferrocene derivatives have the characteristics of aromaticity, low toxicity, stability and biological activity, and are good liquid crystal materials, conductive materials and magnetic materials, especially in material chemistry, electrochemistry and asymmetric synthetic chemistry. There is great interest, and its application prospects are becoming more and more promising. In recent years, thiadiazole compounds have shown outstanding activity in pesticides, and can be used as fungicides, plant growth regulators, insecticides and herbicides. Therefore, this kind of compound has become a hot research topic of "green pesticide" now, which has aroused people's increasing research interest. There are many reports on the synthesis and applicatio...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
CPCY02P20/10
Inventor 刘玉婷刘蓓蓓尹大伟吕博张晓莉杨阿宁王金玉宋思梦
Owner SHAANXI UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com