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

Method for preparing 2-cyanoacet-5-substituted thiophenes compound

A compound, cyanoacetyl technology, applied in the field of synthesis and preparation of organic compounds, can solve problems such as unsatisfactory and difficult product purification, and achieve the effects of convenient operation, high purity and high yield

Active Publication Date: 2009-04-01
CHINA GATEWAY PHARMA DEV CO LTD
View PDF0 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the product is a mixture of 2-cyanoacetylthiophene and 2-cyanoacetyl-5-substituted thiophene, and the solubility difference between the two compounds in organic solvents is small, the product purification is difficult, which cannot meet the requirements of scientific research and pharmaceutical industry for this type of compound. need

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 2-cyanoacet-5-substituted thiophenes compound
  • Method for preparing 2-cyanoacet-5-substituted thiophenes compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The synthesis of embodiment 1 5-fluorothiophene carbonitrile

[0018] In the three-necked flask of 250 milliliters, install thermometer, stirrer, join iodine (0.11mol) to 5-fluorothiophene formaldehyde (R=F, 0.1mol), dioxane (100ml), ammoniacal liquor (0.8mol) in the mixture. Stir at 60°C, follow and control the reaction time by HPLC. Then add Na 2 S 2 o 3 Unreacted iodine was removed, cooled to 0°C, stirred for 1 hour, and a large amount of crystals were produced. It was then filtered and dried to obtain the product as a pale yellow solid with a yield of 92%.

Embodiment 2

[0019] The synthesis of embodiment 2 5-chlorothiophene carbonitrile

[0020] In the three-necked bottle of 250 milliliters, install thermometer, stirrer, join iodine (0.1mol) to 5-chlorothiophene formaldehyde (R=Cl, 0.1mol), ether (80ml), in the ammoniacal liquor (1.0mol) mixture. Stir at 40°C, follow and control the reaction time by HPLC. Then add Na 2 S 2 o 3 Unreacted iodine was removed, cooled to 0°C, stirred for 1 hour, and a large amount of crystals were produced. It was then filtered and dried to obtain the product as a pale yellow solid with a yield of 93%.

Embodiment 3

[0021] The synthesis of embodiment 3 5-bromothiophene carbonitrile

[0022] In the 250 milliliter three-necked bottle, install thermometer, stirrer, join iodine (0.4mol) to 5-bromothiophene formaldehyde (R=Br, 0.1mol), n-butyl ether (100ml), ammoniacal liquor (1.2mol) in the mixture. Stir at 20°C, follow and control the reaction time by HPLC. Then add Na 2 S 2 o 3 Unreacted iodine was removed, cooled to 0°C, stirred for 1 hour, and a large amount of crystals were produced. It was then filtered and dried to obtain the product as a pale yellow solid with a yield of 95%.

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 method for preparing 2-oxopropionitrile-5-substituted thiophene compounds as shown in the formula C. The method includes the following steps: (1) 5-substituted thiophene formaldehyde , iodin and ammonia shown in the formula A are led to react in an inertia organic solution at the temperature of 0 to 60 DEG C to obtain the 5-substituted thiophenecarbonitrile shown in the formula B; (2) the 5-substituted thiophenecarbonitrile shown in the formula B is led to react with acetonitrile in the inertia organic solution, with the existence of alkali and at the temperature of minus 80 to 0 DEG C; wherein, R represents H, F, Cl, Br, I or CH3. The 2-oxopropionitrile-5-substituted thiophene compounds prepared by the method of the invention have high purity reaching above 98 percent (HPLC purity) and meet the requirements of scientific researches and pharmacy industry. The method provided by the invention is simple; the operation is convenient; the yield is high; the method is suitable for large-scale industrial production, with comparatively high industrial application value.

Description

technical field [0001] The invention relates to the field of synthesis and preparation of organic compounds, in particular to a preparation method of 2-cyanoacetyl-5-substituted thiophenol compounds. Background technique [0002] In recent years, 2-cyanoacetyl-5-substituted thiophenols have been reported as potential antiarthritic agents for the treatment of rheumatoid arthritis (Potential antiarthritic agents.2.Benzoylacetonitriles and beta-aminocinnamononitriles, J.Med.Chem. , 1979, 22, p1385-1389), has received increasing attention. [0003] In the existing disclosed technology, the main synthetic methods of general thiophene carbonitrile and 2-cyanoacetyl-5-substituted thiophene compounds are: [0004] Fang (Direct transformation of aldehydes to nitrogenes using iodine in ammoniawater, Tetrahedron Letters, 2001, 42, p1103-1105) et al. have reported a kind of benzaldehyde compound and 2-thiophene formaldehyde and iodine / ammonia / sodium methylate / methanol System reaction ...

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): C07D333/28C07D333/22
Inventor 刘国斌李原强匡通滔王狄泳张勇
Owner CHINA GATEWAY PHARMA DEV CO LTD
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