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

Method for preparing 3-((aryl sulfydryl/alkyl sulfydryl) methyl) ethylene oxide

A technology of ethylene oxide and aryl mercapto group, applied in the field of preparing 3-methyl) ethylene oxide, can solve problems such as harsh reaction conditions, and achieve the effects of easy separation and purification, simple operation method and high yield

Pending Publication Date: 2022-08-09
CHANGZHOU UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction conditions in the existing methods are relatively harsh, and the obtained compound structures are mostly four-membered, five-membered and six-membered epoxy or azacyclic sulfide compounds, and there are no three-membered oxacyclic sulfide compounds. report

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
  • Method for preparing 3-((aryl sulfydryl/alkyl sulfydryl) methyl) ethylene oxide
  • Method for preparing 3-((aryl sulfydryl/alkyl sulfydryl) methyl) ethylene oxide
  • Method for preparing 3-((aryl sulfydryl/alkyl sulfydryl) methyl) ethylene oxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 2,2-dimethyl-3-phenyl-3-((phenylthio)methyl)oxirane

[0022] 2,2-Dimethyl-3-((phenylthio)methyl)oxirane

[0023]

[0024] Combine 2-methyl-3-phenyl-3-en-2-ol (0.2 mmol, 32.42 mg), 1-(phenylthio)succinimide (0.4 mmol, 82.81 mg) and HFIP (2.0 mL) ) into a 20 mL Schlenk tube fitted with a Teflon cap. Then, the Schlenk tube was reacted at room temperature for 2.5 hours. After that, it was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (PE / EA20 / 1) to give the desired product in 91% yield. NMR data: 1 H NMR (CDCl 3 ,400MHz):δ7.38–7.36(m,2H),7.33–7.28(m,3H),7.25–7.24(m,2H,overlapped with CDCl 3 ), 7.21–7.18 (m, 2H), 7.14–7.11 (m, 1H), 3.55 (d, J=13.0Hz, 1H), 3.40 (d, J=13.0Hz, 1H), 1.51 (s, 3H) ,1.00(s,3H). 13 C NMR (CDCl 3 , 101MHz): δ138.7, 136.6, 129.4, 128.6, 127.8, 127.3, 126.9, 125.9, 68.1, 64.6, 40.5, 22.1, 20.6. MS data: MS(EI): 271.1 (M + ).

Embodiment 22

[0025] Example 22, 2-dimethyl-3-((phenylthio)methyl)-3-(p-tolyl)oxirane

[0026] 2,2-Dimethyl-3-((phenylthio)methyl)-3-(p-toly)oxirane

[0027]

[0028]2-Methyl-3-p-tolyl-3-en-2-ol (0.2 mmol, 35.22 mg), 1-(phenylthio)succinimide (0.26 mmol, 53.82 mg) and HFIP (2.0 mL) into a 20 mL Schlenk tube fitted with a Teflon cap. Then, the Schlenk tube was reacted at room temperature for 2.5 hours. After that, it was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (PE / EA20 / 1) to give the desired product in 56% yield. NMR data: 1 H NMR (CDCl 3 400MHz): δ7.25–7.24 (m, 4H, overlapped with CDCl 3 ), 7.21–7.17 (m, 2H), 7.12–7.10 (m, 3H), 3.53 (d, J=12.9Hz, 1H), 3.37 (d, J=12.8Hz, 1H), 2.32 (s, 3H) ,1.49(s,3H),1.00(s,3H). 13 C NMR (101MHz, CDCl 3 ): δ137.0, 136.7, 135.8, 129.5, 128.7, 128.6, 126.9, 126.0, 68.1, 64.7, 40.7, 22.2, 21.2, 20.7. MS data: MS(EI): 285.1 (M + ).

Embodiment 3

[0029] Example 3: 2,2-Dimethyl-3-((phenylthio)methyl)-3-(p-tert-butylphenyl)oxirane

[0030] 2-(4-(Tert-butyl)phenyl)-3,3-dimethyl-2-((phenythio)methyl)oxirane

[0031]

[0032] 2-Methyl-3-p-tert-butylphenyl-3-en-2-ol (0.2 mmol, 32.42 mg), 1-(phenylthio)succinimide (0.26 mmol, 53.82 mg) and HFIP (2.0 mL) was added to a 20 mL Schlenk tube fitted with a Teflon cap. Then, the Schlenk tube was reacted at room temperature for 2.5 hours. After that, it was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (PE / EA20 / 1) to give the desired product in 59% yield. NMR data: 1 H NMR (CDCl 3 ,400MHz):δ7.34-7.28(m,4H),7.24-7.22(m,2H),7.20-7.16(m,2H),7.14-7.09(m,1H),3.53(d,J=12.9Hz ,1H),3.41(d,J=12.9Hz,1H),1.52(s,3H),1.32(s,9H),1.03(s,3H). 13 C NMR (CDCl 3 , 101MHz): δ150.1, 136.8, 135.7, 129.5, 128.6, 126.7, 125.9, 124.8, 68.1, 64.8, 40.7, 34.5, 31.3, 22.3, 20.8. MS data: MS(EI): 327.1 (M + ).

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 relates to the fields of medicine, organic chemical industry and fine chemical industry, in particular to a method for preparing 3-((aryl sulfydryl / alkyl sulfydryl) methyl) ethylene oxide. According to the method, allyl alcohol and N-(aryl sulfydryl / alkyl sulfydryl) succinimide are taken as raw materials, a metal catalyst or any other additive is not needed, alcohol is taken as a solvent, and a product is obtained through reaction at room temperature for 2.5 hours. A series of functionalized 3-((aryl sulfydryl / alkyl sulfydryl) methyl) ethylene oxide compounds with high yield can be obtained through simple post-treatment of the reaction product. Allyl alcohol and N-(aryl sulfydryl / alkyl sulfydryl) succinimide containing different substituent groups can be used as reaction substrates to obtain the corresponding 3-((aryl sulfydryl / alkyl sulfydryl) methyl) ethylene oxide compound.

Description

technical field [0001] The invention relates to the fields of medicine, organic synthesis and fine chemical industry, in particular to a method for preparing 3-((arylmercapto / alkylmercapto)methyl)oxirane. Background technique [0002] 3-((Arylmercapto / alkylmercapto)methyl)oxirane is an important intermediate in organic synthesis, and its derivatized products have good pharmacological activity and are widely used in medicine and biology. Therefore, the effective synthesis of such compounds has strong application value. (See: Secci, F.; Arca, M.; Frongia, A.; et al. Tetrazole amides as hydrogen-bonding donor catalysts in the chemoselective oxidation of sulphides and disulphides [J]. Catalysis Science & Technology 2014, 4(5): 1407- 1415.). [0003] In the existing reports, the synthesis methods of such compounds are mainly using Acid-catalyzed enantioselective oxysulfonylation of enols with organosulfur reagents was obtained (see: Guan, H.; Wang, N.; Huang, D.S.; etal. Enan...

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): C07D301/02C07D303/34
CPCC07D301/02C07D303/34Y02P20/55
Inventor 孙松柏君雪沙宇李渺高万旭
Owner CHANGZHOU 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