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Method for synthesizing N,N-dialkyl unsaturated amide compounds

A technology for amide compounds and synthesis method, which is applied to the synthesis of N,N-dialkyl unsaturated amide compounds and the synthesis field of amide compounds, and can solve the problems of insufficient substrate sources, corrosive use and reaction yield. It is not high enough to achieve the effect of broad industrial application prospects

Active Publication Date: 2017-02-22
山东瑞博龙化工科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, these existing methods have problems such as insufficient substrate sources, insufficient reaction yields, and the use of corrosive or expensive reagents.

Method used

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  • Method for synthesizing N,N-dialkyl unsaturated amide compounds
  • Method for synthesizing N,N-dialkyl unsaturated amide compounds
  • Method for synthesizing N,N-dialkyl unsaturated amide compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0037]

[0038] At room temperature, in an appropriate amount of organic solvent (a mixture of dimethyl sulfoxide (DMSO) and acetonitrile at a volume ratio of 1:2), add 100 mmol of the above formula (I) compound, 140 mmol of the above formula (II) compound, 20 mmol of the Catalyst (being 10mmol bis(triphenylphosphine) cyclopentadienyl ruthenium chloride and 10mmol iron acetylacetonate (Fe(acac) 3 ) mixture), 160mmol oxidant 2-iodobenzoic acid (IBX), 200mmol base tetramethylethylenediamine (TMEDA), 10mmol auxiliary agent 5,5'-dimethyl-2,2'-bipyridine and 20mmol Accelerator cuprous trifluoromethanesulfonate (CuOTf), then stirred and warmed up to 70 ° C, and stirred and reacted at this temperature for 9 hours;

[0039] After the reaction, filter, adjust the pH value of the filtrate to neutral, and fully wash 2-3 times with deionized water, combine the organic phases, dry over anhydrous magnesium sulfate, concentrate under reduced pressure, and the residue is subjected to silic...

Embodiment 2

[0042] Reaction formula is with embodiment 1, and concrete reaction process is as follows:

[0043]At room temperature, in an appropriate amount of organic solvent (a mixture of dimethyl sulfoxide (DMSO) and acetonitrile at a volume ratio of 1:2), add 100 mmol of the above formula (I) compound, 200 mmol of the above formula (II) compound, 10 mmol of the bimetallic Catalyst (being 5mmol bis(triphenylphosphine) cyclopentadienyl ruthenium chloride and 5mmol iron acetylacetonate (Fe(acac) 3 ) mixture), 250mmol oxidant 2-iodoxybenzoic acid (IBX), 100mmol base tetramethylethylenediamine (TMEDA), 20mmol auxiliary agent 5,5'-dimethyl-2,2'-bipyridine and 10mmol Accelerator cuprous trifluoromethanesulfonate (CuOTf), then stirred and heated up to 100 ° C, and stirred and reacted at this temperature for 6 hours;

[0044] After the reaction, filter, adjust the pH value of the filtrate to neutral, and fully wash 2-3 times with deionized water, combine the organic phases, dry over anhydrous...

Embodiment 3

[0047] Reaction formula is with embodiment 1, and concrete reaction process is as follows:

[0048] At room temperature, add 100mmol of the above formula (I) compound, 170mmol of the above formula (II) compound, 15mmol of the bimetallic Catalyst (being 7.5mmol bis(triphenylphosphine) cyclopentadienyl ruthenium chloride and 7.5mmol iron acetylacetonate (Fe(acac) 3 ) mixture), 205mmol oxidant 2-iodylbenzoic acid (IBX), 150mmol base tetramethylethylenediamine (TMEDA), 15mmol auxiliary agent 5,5'-dimethyl-2,2'-bipyridine and 15mmol Accelerator cuprous trifluoromethanesulfonate (CuOTf), then stirred and warmed up to 80 ° C, and stirred and reacted at this temperature for 7 hours;

[0049] After the reaction, filter, adjust the pH value of the filtrate to neutral, and fully wash 2-3 times with deionized water, combine the organic phases, dry over anhydrous magnesium sulfate, concentrate under reduced pressure, and the residue is subjected to silica gel column chromatography, with a...

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Abstract

The invention relates to a method for synthesizing N,N-dialkyl unsaturated amide compounds shown in a formula (III). The method comprises the following steps: reacting a compound of a formula (I) and a compound of a formula (II) in an organic solvent in the presence of a bimetallic catalyst, an oxidizing agent, alkali, aids and a promoter, performing after-treatment after the reaction is ended, so as to obtain the compound of the formula (III). The structural formula is as shown in the specification, wherein R refers to H, C1-C6 alkyl or halogens; R1 and R2 are respectively and independently selected from C1-C6 alkyl; X is halogen. According to the method, due to the specific reaction substrate and unique catalytic reaction system, the target product is obtained at high yield, a brand new synthetic method is provided for the compounds, and the method has wide industrial application prospects.

Description

technical field [0001] The invention relates to a synthesis method of amide compounds, more particularly to a synthesis method of N,N-dialkyl unsaturated amide compounds, belonging to the technical field of organic chemical synthesis. Background technique [0002] Amide compounds can be widely used in various organic chemical reactions, such as nucleophilic addition, cycloaddition, free radical reaction, etc., and they are also important synthetic materials for various bioactive molecules and polymer materials. [0003] As for the unsaturated amide compounds, since there are unsaturated bonds in addition to the amide groups, their applicability in organic synthesis is wider and more subsequent reactions can occur. Therefore, it is necessary to study the synthesis method of unsaturated amides. [0004] So far, the synthetic methods of multiple unsaturated amide compounds have been disclosed or applied in the prior art, for example: [0005] Kristin D. Schleiher et al. ("Nic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/10C07C233/11
CPCC07C231/10C07C233/11
Inventor 不公告发明人
Owner 山东瑞博龙化工科技股份有限公司