Check patentability & draft patents in minutes with Patsnap Eureka AI!

Synthetic method of imidazolinone derivative

An imidazolidinone and a synthesis method technology are applied in the field of synthesis of imidazolidinone derivatives, can solve the problems of high equipment requirements, cumbersome steps, a large amount of waste water, etc., and achieve the effect of meeting synthesis requirements and huge application prospects.

Active Publication Date: 2021-07-09
WUYI UNIV
View PDF5 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above-mentioned synthesis method has the advantages of easy availability of raw materials and low price, it needs to be carried out under high temperature and high pressure conditions, which requires relatively high equipment requirements. Serious environmental pollution and other obvious deficiencies

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
  • Synthetic method of imidazolinone derivative
  • Synthetic method of imidazolinone derivative
  • Synthetic method of imidazolinone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Embodiment 1 of the present invention is: a synthetic method of imidazolinone derivatives, comprising the following steps:

[0069] Add 0.25 mmol benzamidine hydrochloride, 0.375 mmol 1,2-cyclohexanediol, 0.6 mmol cesium carbonate, 60 mg activated carbon supported cobalt metal catalyst (the The mass fraction is 3%) and 1 milliliter of pyridine. After stirring and reacting for 12 hours at 130 ° C under air conditions, stop heating and stirring, cool to room temperature, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by thin layer chromatography to obtain The target product, the stationary phase of the thin-layer chromatography used is silica gel, and the eluent is a mixed solvent of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate=5:1, v / v), and the yield of the product obtained is 89% .

[0070] The hydrogen spectrogram and the carbon spectrogram of the product obtained in Example 1 of the present invention...

Embodiment 2

[0077] Embodiment 2 of the present invention is: a synthetic method of imidazolinone derivatives, comprising the following steps:

[0078] Add 0.25 mmol of 4-methoxybenzamidine hydrochloride, 0.45 mmol of 1,2 cyclohexanediol, 0.5 mmol of potassium hydroxide, 45 mg of cobalt metal catalyst supported on Al2O3 (tri The mass fraction of aluminum oxide is 3%) and 1 milliliter of tert-amyl alcohol. After stirring and reacting for 12 hours at 110° C. under air conditions, stop heating and stirring, cool to room temperature, remove the solvent by rotary evaporation under reduced pressure, and pass through a thin layer Chromatographic separation and purification to obtain the target product, the stationary phase of thin-layer chromatography used is silica gel, and the eluent is a mixed solvent of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate=5:1, v / v), and the obtained The yield of product was 84%.

[0079] The hydrogen spectrogram and the carbon spectrogram of the ...

Embodiment 3

[0086] Embodiment 3 of the present invention is: a synthetic method of imidazolinone derivatives, comprising the following steps:

[0087] Add 0.25 mmol of 4-fluorobenzamidine hydrochloride, 0.5 mmol of 1,2 cyclohexanediol, 0.5 mmol of sodium methoxide, and 60 mg of titanium dioxide-supported nano-cobalt catalyst (the mass fraction of titanium dioxide is 3 %) and 1 milliliter of methanol, after stirring and reacting for 10 hours at 120°C under air conditions, stop heating and stirring, cool to room temperature, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by thin-layer chromatography to obtain the target product. The stationary phase of thin-layer chromatography is silica gel, and the eluent is a mixed solvent of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate=7:1, v / v), and the yield of the obtained product is 83%.

[0088] The hydrogen spectrogram and the carbon spectrogram of the product obtained in Example 3...

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 synthesis method of an imidazolinone derivative. According to the method, amidine compounds and polyhydric alcohol compounds are taken as raw materials, high-value conversion of polyhydric alcohol is catalyzed by a cobalt catalyst to form a series of imidazolinone derivatives, a novel and green synthesis path meeting the sustainable chemical principle is developed, high-value conversion of renewable resources is achieved, and the method is suitable for industrial production. Therefore, the synthesis requirements on the imidazolinone derivative are met. The synthesis method has the advantages of wide substrate applicability, good functional group compatibility and use of a reusable cheap metal catalyst and air as an oxidant, has potential to prepare the imidazolinone derivative in one step on a large scale, and also provides an important way for converting biomass resources into high-value functional molecules.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of imidazolinone derivatives. Background technique [0002] Imidazolinones are a class of nitrogen-containing heterocyclic compounds with good biological and pharmacological activities. They widely exist in natural active products and play an important role in human health and industrial and agricultural production. Many imidazolinone fungicides, herbicides and natural medicines have been discovered. [0003] Due to their encouraging properties, the construction of imidazolinone derivatives has been an attractive topic in the scientific community. The conventional method about imidazolinone functional molecule in the related art relates to following several reactions: (1) the cyclization reaction of diamide compound; (2) the cyclization condensation reaction of amino ester and cyanamide; (3) 1 , Intermolecular condensation ring reaction ...

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): C07D235/02C07D401/04C07D233/70
CPCC07D235/02C07D401/04C07D233/70
Inventor 谢锋张向宇林世卓罗楚君陈灵容陈晓勇
Owner WUYI UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com