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

Preparation method of benzodithiocyclopentadiene derivatives

A technology of benzodithiocyclopentadiene and derivatives, which is applied in the field of preparation of benzodithiocyclopentadiene derivatives, can solve the problems of narrow substrate range, harsh reaction conditions, and lack of practical value, and achieves Easy separation and purification, rich synthesis methods, green and environmental protection effect of the reaction system

Active Publication Date: 2021-03-16
XUZHOU NORMAL UNIVERSITY
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these disclosed catalytic systems usually use thiophenol or its derivatives with pungent smell as "sulfur source", and they also generally have many shortcomings such as narrow substrate scope, harsh reaction conditions, low product yield, etc., which lack practicality. value

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 benzodithiocyclopentadiene derivatives
  • Preparation method of benzodithiocyclopentadiene derivatives
  • Preparation method of benzodithiocyclopentadiene derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Preparation of benzodithiocyclopentadiene derivative 2a, the experimental results are shown in Table 1.

[0030]

[0031] To a 50 mL Shrek bottle with a magnetic stirring device was added toluene (10 mL), N-phenyl-2-bromothiobenzamide 1a (0.291 g, 1.0 mmol) and S 8 (0.036g, 1.2mmol), add cuprous iodide (0.019g, 0.1mmol), 1,10-phenanthroline (0.036g, 0.2mmol), cesium carbonate (0.326g, 1.0mmol) after stirring, will It was placed in a 100°C oil bath and continued to stir. TLC detects that the substrate disappears, and the reaction ends. The reaction solution was poured into saturated aqueous sodium chloride solution (10 mL), extracted with dichloromethane (3×10 mL), and the organic phases were combined, then backwashed with water (3×10 mL), dried over anhydrous calcium chloride, Steps such as suction filter, vacuum distillation obtain viscous solid, finally through silica gel column chromatography (eluent is V 石油醚 :V 乙酸乙酯 =20:1) A yellow solid was obtain...

Embodiment 2

[0035] Replace 1a in Example 1 with 1b, wherein the amount of each material is: 1b (0.306g, 1.0mmol) and S 8 (0.036g, 1.5mmol), add cuprous iodide (0.19g, 1mmol), 1,10-phenanthroline (0.108g, 0.6mmol), cesium carbonate (0.65g, 2.0mmol); The non-aqueous solvent Select DMF (10 mL).

[0036] Other conditions are the same as Example 1, and the experimental results are shown in Table 1.

[0037]

[0038] Spectrum analysis data 2b:

[0039] Yellow solid, m.p.164-165℃; 1 H-NMR (400MHz, CDCl 3 )δ8.15(d,J=8.8Hz,1H),7.47-7.42(m,2H),7.32-7.28(m,1H),7.21(d,J=8.0Hz,2H),7.05(d,J =7.2Hz, 2H), 2.35(s, 2H); 13 C-NMR (CDCl 3,100MHz)δ164.8,147.9,144.2,133.8,131.7,130.7,129.2,125.7,124.4,122.3,118.8,20.0; HRMS(APCI)m / z calculated for C 14 h 11 NS 2 [M+H] + :258.0406found:258.0411.

Embodiment 3

[0041] Replace 1a in Example 1 with 1c, wherein the amount of each material is: 1c (0.312g, 1.0mmol) and S 8 (0.072g, 3mmol), add cuprous iodide (0.19g, 1mmol), 1,10-phenanthroline (0.18g, 1mmol), cesium carbonate (0.65g, 2.0mmol); Described non-aqueous solvent selects DMF (10 mL).

[0042] Other conditions are the same as Example 1, and the experimental results are shown in Table 1.

[0043]

[0044] Spectral analysis data 2c:

[0045] Yellow solid, m.p.173-174℃; 1 H-NMR (400MHz, CDCl 3 )δ8.18-8.15(m,1H),7.52-7.47(m,2H),7.37-7.33(m,1H),7.16-7.12(m,2H),6.99-6.95(m,2H),3.84( s,3H); 13 C-NMR (CDCl 3 ,100MHz)δ165.6,157.1,145.1,144.7,132.9,131.7,126.8,125.5,123.4,121.4,114.8,55.5; HRMS(APCI)m / z calculated for C 14 h 11 NOS 2 [M+H] + :274.0355found:274.0381.

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 a benzodithiocyclopentadiene derivative. Benzodithiocyclopentadiene is synthesized by reacting S8 as a sulfur source with 2-bromothioamide. The synthesis method provides a cheap, easily available and environment-friendly synthesis method for synthesis of benzodithiocyclopentadiene compounds, adopts a green and environment-friendly reaction system, obtains products easy to be separated and purified, is suitable for synthesizing various highly functionalized benzodithiocyclopentadiene compounds, is particularly suitable for large-scale industrial production, and can prepare high-purity benzodithiocyclopentadiene compounds at high efficiency and high yield.

Description

technical field [0001] The invention belongs to organic synthesis chemistry technology, in particular to a preparation method of benzodithiocyclopentadiene derivatives. Background technique [0002] Benzodithiocyclopentadiene (BDT) is a class of molecules with good biological activity, often showing strong anti-hepatitis B virus (J Labeled Compd Rad.2012,55,197), anti-mycobacterium tuberculosis (Bioorg Med ChemLett.2008,18,3706) and anti-diarrheal activity (J.Med.Chem.2004,47,5265). At the same time, as an important intermediate of fine chemical products, benzodithiocyclopentadiene has a wide range of uses in the fields of food, pesticides, daily chemicals, coatings, textiles, printing and dyeing, papermaking, photosensitive materials, and polymer materials. However, only a very small amount of benzodithiocyclopentadiene compounds can be isolated from natural substances, and the cost is expensive. Therefore, the artificial synthesis of these substances is therefore of part...

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 Patents(China)
IPC IPC(8): C07D339/04C07D495/04
CPCC07D339/04C07D495/04
Inventor 吕兰兰黄梦乔刘建全王香善
Owner XUZHOU NORMAL UNIVERSITY
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