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

Green synthesis method of benzothiazole heterocyclic compound

A heterocyclic compound, benzothiazole technology, applied in the field of chemical synthesis, to achieve the effect of low requirements, wide application range and low price

Inactive Publication Date: 2013-12-18
WENZHOU UNIVERSITY
View PDF4 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still many disadvantages in these methods, such as the use of complexes of noble metals Ru, Ir, etc. as catalysts, the use of expensive ligands, the use of a large amount of dehydrogenation reagents such as active olefins, or the need for inert gas protection and high temperature. carry on, wait

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
  • Green synthesis method of benzothiazole heterocyclic compound
  • Green synthesis method of benzothiazole heterocyclic compound
  • Green synthesis method of benzothiazole heterocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of 2-phenylbenzothiazole from benzyl alcohol and o-aminothiophenol

[0020]

[0021] Add t-BuONa (0.0192g, 20mol%), benzyl alcohol (1.5mmol, 1.5equiv.) and o-aminothiophenol (0.1252g, 1.0mmol,) to the reaction tube in sequence, then add toluene (1.0mL) as solvent , Add an air balloon at normal pressure, heat to 100°C and react for 24h. After the completion of the reaction monitored by TLC, the product was separated and purified by column chromatography, and the separation yield was 82%. 1 HNMR (500MHz, CDCl 3 ):δ8.11-8.07(m,3H),7.91-7.90(m,1H),7.51-7.48(m,4H),7.40-7.37(m,1H). 13 CNMR (125.4MHz, CDCl 3 ): δ168.1, 154.1, 135.0, 133.6, 131.0, 129.0, 127.5, 126.3, 125.2, 123.2, 121.6. MS (EI): m / z (%) 212 (17), 211 (100), 210 (22), 184(6), 108(24), 106(6), 92(5), 82(8), 69(13), 63(6), 58(4).

Embodiment 2

[0023] Preparation of 2-(2-chloro)phenylbenzothiazole from 2-chlorobenzyl alcohol and o-aminothiophenol

[0024]

[0025] In the reaction tube, add t-BuONa (0.0192g, 20mol%), 2-chlorobenzyl alcohol (1.5mmol, 1.5equiv.) and o-aminothiophenol (0.1252g, 1.0mmol.), then add toluene (1.0mL ) as the solvent, plus atmospheric pressure air balloons, heated to 100 ° C for 24 hours. After the completion of the reaction was monitored by TLC, the product was separated and purified by column chromatography, and the separation yield was 89%. 1 HNMR (500MHz, CDCl 3 ):δ8.22-8.20(m,1H),8.13(d,J=8.5Hz,1H),7.94(d,J=8.0Hz,1H),7.53-7.50(m,2H),7.44-7.39( m,3H). 13 CNMR (125.4MHz, CDCl 3 ): δ164.1, 152.4, 136.1, 132.7, 132.2, 131.7, 131.1, 130.8, 127.1, 126.2, 125.4, 123.4, 121.3. MS (EI): m / z (%) 246 (19), 245 (100), 244 (9), 210(20), 209(8), 183(6), 108(32), 105(8), 82(11), 69(18), 63(7), 58(6).

Embodiment 3

[0027] Preparation of 2-(3-chloro)phenylbenzothiazole from m-chlorobenzyl alcohol and o-aminothiophenol

[0028]

[0029] Add t-BuONa (0.0192g, 20mol%), m-chlorobenzyl alcohol (1.5mmol, 1.5equiv.) and o-aminothiophenol (0.1252g, 1.0mmol.) in turn to the reaction tube, then add toluene (1.0mL) As a solvent, add an air balloon at atmospheric pressure, and heat to 100 ° C for 24 hours. After the reaction was complete as monitored by TLC, the product was separated and purified by column chromatography, and the separation yield was 81%. 1 HNMR (500MHz, CDCl 3 ):δ8.12(t,J=1.5Hz,1H),8.08(d,J=8.0Hz,1H),7.95-7.90(m,2H),7.53-7.49(m,1H),7.47-7.39( m,3H). 13 CNMR (125.4MHz, CDCl 3 ): δ166.3, 153.9, 135.2, 135.1, 135.0, 130.8, 130.2, 127.4, 126.5, 125.7, 125.5, 123.4, 121.7. MS (EI): m / z (%) 246 (18), 245 (100), 244 (9), 210(14), 209(5), 123(5), 108(28), 105(8), 69(17), 63(6), 58(5).

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 green synthesis method of a benzothiazole heterocyclic compound. Alcohol and aminothiophenol compounds are directly subjected to an oxidative condensation cyclization reaction to synthetize the benzothiazole heterocyclic compound in air under the condition of taking a water-soluble inorganic base as a catalyst and air as an oxidizing agent. By adopting the method, alcohols which are cheap and available, wide in source, stable, and low in toxicity are taken as raw materials; a water-soluble non-transition metal catalyst which is low in price is used; air which is convenient to use, economic and safe is directly utilized as the oxidizing agent, so as to obtain a target heterocyclic compound by air alcohol oxidation and cyclic condensation synthesis. The method is simple and mild in reaction condition, free of protection of inert gases, and easy to operate, and is carried out in air; the only by-product is water; separation and purification of the product are simple and easy; the recovery rate is high. The method is low in demands on reaction conditions, and wide in application range, and has good research and industrial application prospects.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a green method for directly preparing benzothiazole heterocyclic compounds through aerobic alcohol oxidation and condensation cyclization under air under the catalysis of alcohol and o-aminothiophenol under the catalysis of a non-transition metal catalyst. Background technique [0002] Substituted benzothiazole heterocycles and their derivatives have heterocyclic structures with pharmaceutical activity and biochemical activity such as thiazole, and many derivatives can be used to treat diabetes, Alzheimer's disease, or have anti-tumor activity, so these heterocyclic structures It plays an important role in many fields such as drug synthesis and biopharmaceuticals, and is a very important drug synthesis intermediate. Benzothiazole compounds and their derivatives can generally be prepared by dehydration condensation of o-aminothiophenol and acid, or deamination condens...

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): C07D277/66C07D417/04
Inventor 徐清史鑫康郭俊梅周斌
Owner WENZHOU 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