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

Microwave radiation synthesis of 1,3-substituted imidazole-2-thioketone

A technology of disubstituted imidazole and microwave radiation, applied in the direction of organic chemistry, can solve the problems of long reaction time and methanol poisoning, and achieve the effect of simple treatment and simple reaction operation.

Inactive Publication Date: 2007-02-14
ZHEJIANG UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Arduengo applied for a patent (USP5,104,993) for the synthesis of 1,3-dialkylimidazolium-2-thiones in 1992. This synthesis method is in the presence of potassium carbonate, with 1,3-alkylimidazolium salt and Sulfur is used as a raw material to synthesize 1,3-dialkylimidazole-2-thione, the reaction time is long (24-48 hours) and anhydrous is required, and methanol is highly toxic

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
  • Microwave radiation synthesis of 1,3-substituted imidazole-2-thioketone
  • Microwave radiation synthesis of 1,3-substituted imidazole-2-thioketone
  • Microwave radiation synthesis of 1,3-substituted imidazole-2-thioketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Example 1 Synthesis of 1,3 dimethylimidazole-2-thione

[0014] Mix 10 mmol 1,3-dimethylimidazole chloride and 11 mmol potassium thioacetate in a 20 ml single-necked bottle evenly, install a reflux condenser, and react under 150W power microwave radiation for 5 minutes, naturally After cooling to room temperature, the reaction mixture was dissolved with 50 ml of ethyl acetate-water (volume ratio 1:1), placed in a separatory funnel, and the organic phase was separated, dried with anhydrous potassium sulfate for 2 hours, concentrated, and washed with silica gel. Column chromatography (eluent: n-hexane: ethyl acetate = 2:1) gave 998 mg of 1,3-dimethylimidazole-2-thione with a yield of 75%.

[0015]

[0016] 1 HNMR (500MHz, CDCl 3 ): δ=3.60(s, 6H), 6.71(s, 2H);

[0017] 13 CNMR (500MHz, CDCl 3 ): δ=34.56, 117.55, 162.12;

[0018] IR (cm -1 )2957, 1445, 1230, 1045;

[0019] MS([M+H] + ): 128.8;

Embodiment 2

[0020] Example 2 Synthesis of 1,3-dimethylimidazole-2-thione

[0021] The reaction steps are the same as in Example 1, except that 1,3-dimethylimidazole bromide is used as the raw material to obtain the product with a yield of 78%.

Embodiment 3

[0022] Example 3 Synthesis of 1,3-dimethylimidazole-2-thione

[0023] The reaction steps are the same as in Example 1, except that 1,3-dimethylimidazolium tetrafluoroborate is used as the raw material to obtain the product with a yield of 79%.

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

PropertyMeasurementUnit
poweraaaaaaaaaa
Login to View More

Abstract

Synthesis of 1,3-dibasic imidazole-2-thio-ketone by micro-wave radiation is carried out by taking 1,3-dibasic imidazole onium salt and potassium thiacetic with amount ratio 1:1-3, synthesizing 1,3-dibasic imidazole-2-thio-ketone with power 50-300W and reacting time 2-20mins, extracting, filtering, washing and concentrating. R1=alkyl(C1-4), benzyl, R2=alkyl(C1-4), benzyl, allyl, ethoxyl, and acetoxy ethyl. Its advantages include fast reacting speed, simple operation and after treatment, and no pollution.

Description

technical field [0001] The invention relates to a method for synthesizing 1,3-disubstituted imidazole-2-thione by microwave radiation. Background technique [0002] Imidazole-2-thione is a class of important compounds widely used in medicine and chemical industry, such as 1-methylimidazole-2-thione (Methimazole  ) can be used to treat thyroid secretion disorders; some imidazole-2-thiones can also be used to treat arthritis. In addition, imidazole thione has antioxidant and flame retardant functions, such as benzimidazole thione can be used as rubber antioxidant; 1,3-dialkylimidazole-2-thione can be used as a catalyst for the synthesis of epoxy resin and can significantly improve properties of the resin. Arduengo applied for a patent (USP5,104,993) for the synthesis of 1,3-dialkylimidazolium-2-thiones in 1992. This synthesis method is in the presence of potassium carbonate, with 1,3-alkylimidazolium salt and Sulfur is used as a raw material to synthesize 1,3-dialkylimidaz...

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): C07D233/84
Inventor 雷鸣王彦广
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