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

Method for promoting acylation of amine or alcohol by carbon dioxide

A carbon dioxide and acylation technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of harsh reaction conditions, long reaction time, cumbersome operation, etc., and achieve mild reaction conditions, simple operation, and economical The effect of the preparation method

Active Publication Date: 2021-05-28
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
View PDF3 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of the above reagents often brings problems such as long reaction time, cumbersome operation, harsh reaction conditions, and toxicity. Therefore, it is of great scientific significance to explore and develop new methods that can realize esterification reactions under mild conditions.

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 promoting acylation of amine or alcohol by carbon dioxide
  • Method for promoting acylation of amine or alcohol by carbon dioxide
  • Method for promoting acylation of amine or alcohol by carbon dioxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Dissolve 0.2 mmol of an amine reaction substrate such as N-methylaniline in 1 mL of ethylene glycol dimethyl ether, then add 3 equivalents of potassium carboxylate or potassium thiocarboxylate, and react under a carbon dioxide (1 atm) atmosphere React at 35°C for 8 h, cool to room temperature, pour the reaction mixture into 10 mL of water, extract three times with 10 mL of ethyl acetate, combine the organic phases and wash with 15 mL of saturated brine, dry the organic phase over anhydrous sodium sulfate, and remove the organic phase by rotary evaporation. Solvent, the crude product is purified through a section of about 10 cm long silica gel chromatography column (petroleum ether: ethyl acetate = 20:1~2:1) to obtain the corresponding amide compound 3a, compound 3b, compound 3c, and compound 3d respectively , Compound 3e, Compound 3f, Compound 3g, Compound 3h, Compound 3i, Compound 3j, Compound 3k, Compound 3l, Compound 3m, Compound 3n, Compound 3o, Compound 3p, Compound...

Embodiment 2

[0180] Dissolve 0.2 mmol of a phenolic reaction substrate such as phenol in 1 mL of γ-valerolactone, then add 3 equivalents of potassium thioacetate, react in a carbon dioxide (1 atm) atmosphere at 100oC for 14 hours, cool to room temperature, and The mixture was poured into 10 mL of water, extracted three times with 10 mL of ethyl acetate, the organic phases were combined and washed with 15 mL of saturated brine, after drying the organic phase with anhydrous sodium sulfate, the organic solvent was removed by rotary evaporation, and the crude product was passed through a section of about 10 cm long silica gel Chromatographic column (petroleum ether: ethyl acetate = 20:1 ~ 2:1) was purified to obtain the corresponding ester compound 5a, compound 5b, compound 5c, compound 5d, compound 5e, compound 5f, compound 5g, compound 5h , Compound 5i, Compound 5j, Compound 5k, Compound 5l, Compound 5m, Compound 5n.

[0181] Spectral data are as follows:

[0182]

[0183] o-tolyl acetat...

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 a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.

Description

technical field [0001] The invention relates to the technical field of synthesis of amide compounds and ester compounds, in particular to a carbon dioxide-promoted acylation method of amines or alcohols. Background technique [0002] Amides and esters are two important classes of chemicals, and the acylation of amines and alcohols is an important method for the preparation of these two classes of compounds, respectively. The amide bond is not only the basic structural unit of many natural products (such as peptides, proteins, etc.), but also an important functional group in chemical molecules, widely present in catalysts, pharmaceuticals, agricultural chemicals and polymers. [0003] The traditional preparation method of amides often requires the use of acylating reagents such as acid chlorides or acid anhydrides, the reaction is sensitive to water, and acid chlorides or acid anhydrides have a pungent odor (see: CN1035873C). Thiocarboxylic acid is a new type of acylating ag...

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): C07C231/02C07C233/58C07C233/07C07D209/08C07D307/52C07D215/08
CPCC07C231/02C07D209/08C07D307/52C07D215/08C07C233/58C07C233/07
Inventor 李跃辉王欢李玉东摆建飞
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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