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

Preparation method of alkali-promoted asymmetric organic persulfide compound

A compound, asymmetric technology, used in the preparation of sulfides, organic chemistry, steroids, etc., can solve the problems of harsh reaction process requirements, complex systems, environmental pollution, etc. simple effect

Active Publication Date: 2021-04-30
ZHEJIANG UNIV
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method system is complicated, and the material ratio of the raw material sodium thiosulfate, halogenated hydrocarbon and sodium sulfinic acid is high, and the one-pot reaction cannot be realized
[0008] There are many deficiencies in the above methods: the reagents used in the reaction are highly toxic or corrosive, the raw materials are not easy to obtain, the reaction process is demanding, the production cost is high, and the environment is polluted.

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
  • Preparation method of alkali-promoted asymmetric organic persulfide compound
  • Preparation method of alkali-promoted asymmetric organic persulfide compound
  • Preparation method of alkali-promoted asymmetric organic persulfide compound

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0067] Synthesis of reference example 1 raw material formula (II) compound

[0068]

[0069] Among them, R 2 , Ring A is as defined in the present invention; Y is Cl or Br.

[0070] Add 4 mL of acetonitrile to a 10 mL two-neck Schlenk tube. Compound of formula (IV-1) (0.5 mmol) and compound of formula (V) (1.5 equivalents, 0.75 mmol) were added, and the reaction mixture was reacted at 100°C for 3 h, then turned to room temperature, and stirred overnight. Filtrate and concentrate the filtrate to obtain a crude product, which is separated by column chromatography to obtain a compound of formula (II).

reference example 2

[0071] Reference example 2 synthesis of raw material formula (II) compound

[0072]

[0073] Among them, R 2 , Ring A is as defined in the present invention.

[0074] Dissolve the compound of formula (IV-2) (1 equivalent) in acetonitrile, add the compound of formula (V) (1.5 equivalents), NBS (2.0 equivalents) and stir at room temperature, monitor the reaction by TLC, until the raw material disappears, add brine and ethyl acetate, the organic layer was separated, the aqueous phase was extracted with ethyl acetate, the combined organic layer was washed with brine, and washed with Na 2 SO 4 Drying and evaporation in vacuo afforded a crude product of the compound of formula (II-2), which was separated by column chromatography to give the compound of formula (II).

Embodiment 1

[0076]

[0077] In a dry 25 mL Schlenk reaction tube, add 0.5 mmol of 4-methoxyphenyl thiosulfonate, 1.0 mmol of thiourea, 1.0 mmol of benzyl bromide, 0.5 mmol of potassium carbonate, and 3 mL of toluene. Stir at 80°C for 24 hours. After the reaction, cool to room temperature, filter, concentrate the filtrate, and directly pass through a silica gel column (the volume ratio of ethyl acetate to petroleum ether is 1:50-1:3) to obtain the product with a yield of 92%.

[0078] 1 H NMR (400MHz, CDCl 3 )δ7.36–7.27(m,5H),7.18–7.15(m,2H),6.87–6.85(m,2H),3.81(s,3H),3.65(s,2H),3.57(s,2H) ; 13 C NMR (100MHz, CDCl 3 ) δ 159.0, 137.4, 130.5, 129.4, 129.2, 128.4, 127.4, 113.8, 55.2, 43.3, 42.7.

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 preparation method of an asymmetric organic persulfide compound. The preparation method comprises the following step: under the promotion of alkali, carrying out one-pot reaction on a compound shown in a formula (I), a compound shown in a formula (II) and thiourea to obtain the asymmetric organic persulfide compound shown in a formula (III). The preparation method is mild in reaction condition, easy to operate and high in yield. The preparation method can be used for preparing organic persulfide compounds and realizing the overvulcanization modification of pharmaceutical molecules such as acetaminophen and estrone and natural product molecules such as zingiberone and amino acid.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of an asymmetric organic persulfur compound. Background technique [0002] Asymmetric organic persulfur compounds are a class of sulfur-containing organic compounds with extremely high medical value. Currently commercially available sulfur-containing drugs, such as prothiolamine, furathiamine, and romidepsin, all have sulfur bridges . In natural product chemistry, more than 120 polythiodiketopiperazines and their derivatives have been discovered, and their good anti-inflammatory and antibacterial effects have also attracted the attention of medicinal chemists. At the same time, in the research of targeted drugs, this compound with disulfide bonds is a good carrier for drug delivery and release. For this reason, chemists have intensified their efforts in the development of asymmetric organic persulfur compounds in recent years. [0003] At present, the meth...

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): C07C319/14C07C323/16C07C323/56C07C323/65C07C323/09C07C323/20C07C323/42C07C323/12C07D333/34C07D209/48C07C323/52C07D215/227C07D215/12C07D311/18C07D309/04C07J31/00C07D307/79C07D211/24C07C323/59
CPCC07C319/14C07D209/48C07D211/24C07D215/12C07D215/227C07D307/79C07D309/04C07D311/18C07D333/34C07J31/006C07C2602/08C07C323/16C07C323/56C07C323/65C07C323/09C07C323/20C07C323/42C07C323/12C07C323/52C07C323/59
Inventor 潘远江王敦盖
Owner ZHEJIANG UNIV
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