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Novel method for synthesizing N-substitute amide derivative

A technology of amide derivatives and a new method, which is applied in the preparation of organic compounds, the formation/introduction of amide groups, the preparation of carboxylic acid amides, etc., can solve the problems of high reaction temperature, limited substrate range, cumbersome operation process, etc. Simple operation, easy product separation and high reaction efficiency

Inactive Publication Date: 2017-08-18
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Although multiple methods for synthesizing N-substituted amide derivatives have been disclosed in the prior art, there are more or less defects in these methods, for example: metals or other substances are required as catalysts or accelerators, and additional ligands are required. The process is cumbersome, the reaction temperature is high, the substrate range is limited, etc., which do not meet the requirements of green environmental protection

Method used

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  • Novel method for synthesizing N-substitute amide derivative
  • Novel method for synthesizing N-substitute amide derivative
  • Novel method for synthesizing N-substitute amide derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] At room temperature, add 0.2 mmol of the compound represented by formula (I-1) and 1 ml of formamide into a reaction tube equipped with a stirring magnet, stir and raise the temperature to 120° C., and react at this temperature for 15 h.

[0038] After the reaction, the reaction solution was cooled to room temperature, 15ml of ethyl acetate and 15ml of water were added, the organic layer was washed with 15ml of saturated ammonium chloride solution and 15ml of saturated sodium chloride solution, dried over anhydrous sodium sulfate for 1 hour, and covered with a layer of Silica gel funnel was used for filtration, and then the solvent was distilled off under reduced pressure, and the residue was purified by thin-layer chromatography silica gel plate (20cm×20cm) to obtain the target product represented by formula (III-1).

[0039] After calculation, the yield of the target product represented by formula (III-1) is 99%.

[0040] NMR data: 1 H NMR (500MHz, CDCl ...

Embodiment 2

[0043]

[0044] At room temperature, add 0.2 mmol of the compound represented by formula (I-2) and 1 ml of formamide into a reaction tube equipped with a stirring magnet, stir and raise the temperature to 120° C., and react at this temperature for 15 h.

[0045] After the reaction, the reaction solution was cooled to room temperature, 15ml of ethyl acetate and 15ml of water were added, the organic layer was washed with 15ml of saturated ammonium chloride solution and 15ml of saturated sodium chloride solution, dried over anhydrous sodium sulfate for 1 hour, and covered with a layer of Silica gel funnel was used for filtration, and then the solvent was distilled off under reduced pressure, and the residue was purified by thin-layer chromatography silica gel plate (20cm×20cm) to obtain the target product represented by formula (III-2).

[0046] After calculation, the yield of the target product represented by formula (III-2) is 74%.

[0047] NMR data: 1 H NMR (500MHz, CDCl 3 ...

Embodiment 3

[0050]

[0051] At room temperature, add 0.2 mmol of the compound represented by formula (I-3) and 1 ml of formamide into a reaction tube equipped with a stirring magnet, stir and raise the temperature to 120° C., and react at this temperature for 15 h.

[0052] After the reaction, the reaction solution was cooled to room temperature, 15ml of ethyl acetate and 15ml of water were added, the organic layer was washed with 15ml of saturated ammonium chloride solution and 15ml of saturated sodium chloride solution, dried over anhydrous sodium sulfate for 1 hour, and covered with a layer of Silica gel funnel was used for filtration, and then the solvent was distilled off under reduced pressure, and the residue was purified by thin-layer chromatography silica gel plate (20cm×20cm) to obtain the target product represented by formula (III-3).

[0053] After calculation, the yield of the target product represented by formula (III-3) is 55%.

[0054] NMR data: 1 H NMR (500MHz, CDCl ...

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Abstract

The invention discloses a novel method for synthesizing an N-substitute amide derivative. The novel method is characterized by comprising the steps that at the air atmosphere, no catalyst or alkali or other any additives are added, an organic amine compound shown in a formula (I) is adopted as a reaction substrate, a solvent shown in a formula (II) is adopted as an acylation reagent, an acylation reaction is performed under the reaction temperature of 120-150 DEG C to generate the N-substitute amide derivative shown in a formula (III), and the equation is shown in the description. The novel method has the advantages that environmental protection is achieved, and post-treatment and product separation are easy; the range of the substrate is wide, and the substrate can be primary amine and can also be secondary amine; the solvent can be amide and can also be carboxylic acid, and the solvent can be adopted as the acylation reagent to participate in the reaction; the reaction efficiency is high, and the majority of reactions can reach the quantified yield; water and air have no effect on the reaction, inert gas shielding is not needed, and operation is easy.

Description

technical field [0001] The invention relates to a new method for synthesizing N-substituted amide derivatives, in particular to a chemical reaction between an organic amine compound and an aliphatic amide or carboxylic acid, and belongs to the technical field of organic synthesis chemistry. Background technique [0002] Amide compounds are an important class of compounds in natural products, because the amide structure is the backbone of polypeptides and proteins, and in the fields of industrial chemistry and medicinal chemistry, the amide structure is also an important functional group structure. Amide compounds are widely used in organic synthesis, biology, and polymer synthesis. As shown below, nylon 66, which is widely used in the plastics industry, and the non-addictive pure hypnotic drug zolpidem contain amide bond. [0003] [0004] Due to the important application of amide compounds in biology, medicine and industrial production, the efficient synthesis of amide ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/06C07C231/10C07C233/03C07C233/15C07C233/33C07C233/07C07C233/05C07D213/75C07D217/06C07D209/08
CPCC07B43/06C07C231/10C07D209/08C07D213/75C07D217/06C07C233/03C07C233/15C07C233/33C07C233/07C07C233/05
Inventor 夏远志贾萌萌林波
Owner WENZHOU UNIVERSITY
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