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Preparation method of amide

A technology of amides and compound amides, which is applied in the field of amides preparation, can solve the problems of large toxic chemical substances or by-products, and achieve the effects of wide application of substrates, cost reduction, and good development prospects

Active Publication Date: 2022-07-19
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods often employ stoichiometric coupling agents and additives, which generate large amounts of toxic chemicals or by-products

Method used

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preparation example Construction

[0029] A preparation method of amide, comprising the following steps:

[0030] The compound of formula (I) and the compound of formula (II) are dissolved in an organic solvent and reacted in an oxygen atmosphere at a temperature of ≥110 ° C to prepare the compound of formula (III) amide; and / or

[0031] The compound of formula (IV) and the compound of formula (II) are dissolved in an organic solvent, and the reaction is carried out at a temperature of ≥110 ° C in an oxygen atmosphere to prepare the compound of formula (III) amide;

[0032] The structures of the compound of formula (I), compound of formula (II), compound of formula (III) and compound of formula (IV) are as follows:

[0033]

[0034] It can be understood that under the action of oxygen, isothiocyanates or isocyanates and aldehydes can generate amides at temperatures ≥110°C.

[0035] In some of these embodiments, in the preparation method of the amide, the organic solvent is selected from the group consisting...

Embodiment 1

[0055] In a 10 mL sealed tube, add isothiocyanate (0.2 mmol), aldehyde (2 mmol), dichloroethane (0.25 mL, 0.8 M), O 2, and reacted at 115°C for 36h. Monitored by TLC, the reaction was stopped until the isothiocyanate reaction was complete. Extracted with ethyl acetate and water, the organic phase was dried over anhydrous sodium sulfate and spin-dried, the collected crude product was purified by column chromatography [eluent: petroleum ether: ethyl acetate=10:1 (v / v)], Product 1-1 was collected in 86% yield.

[0056]

[0057] White solid, mp127-128℃. 1 H NMR (400MHz, CDCl 3 )δ7.55(d,J=7.7Hz,2H),7.38(s,1H),7.31(t,J=7.9Hz,2H),7.10(t,J=7.4Hz,1H),2.08–2.01( m, 1H), 1.77–1.66 (m, 2H), 1.61–1.50 (m, 2H), 0.95 (t, J=7.4Hz, 6H). 13 C NMR (100 MHz, CDCl 3 )δ174.4,138.0,129.0,124.2,120.0,52.4,25.9,12.1.HRMS(ESI): Calcd for C 12 H 18 NO[M+H] + :192.13829;Found:192.13796.

[0058] Yield=molar amount of compound of formula (I-1) / molar amount of phenyl isothiocyanate×100%

Embodiment 2

[0060] Basically the same as Example 1, only the volume of dichloromethane added is different, that is, the concentration is different.

[0061] Phenyl isothiocyanate (0.2 mmol), 2-ethylbutanal (2 mmol), different volumes of dichloroethane (different concentrations) (0.1, 0.3, 0.5, 0.8, 1.0 M) were added to 10 mL of resistant In the pressure tube, O 2 , and reacted at 115 °C for 36 h. Monitored by TLC, the reaction was stopped until the isothiocyanate reaction was complete. Extracted with ethyl acetate and water, the organic phase was dried over anhydrous sodium sulfate and spin-dried, the collected crude product was purified by column chromatography [eluent: petroleum ether: ethyl acetate=10:1 (v / v)], The coupling product I-1 is isolated, and the calculated separation yield is shown in Table 1.

[0062] Table 1 Effects of different concentrations on the coupling reaction

[0063]

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Abstract

The invention relates to a method for preparing an amide. Under the action of oxygen, isothiocyanate and aldehyde can react to form an amide. The effective yield can be obtained only when the reaction temperature is not less than 110°C. This method is also applicable to the reaction of isocyanates and aldehydes to form amides. The preparation method has cheap raw materials, wide substrate applicability, no metal catalyst, initiator or other activator in the reaction process, is green and economical, and can effectively reduce costs.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of an amide. Background technique [0002] Amide compounds are recognized as one of the most functional chemical bonds in the field of organic synthesis. They are widely found in a series of natural products, medicines, agricultural chemicals, polymers and functional materials. They are the basic components of peptide bonds in proteins. The synthesis of amides is of great significance in both medicinal chemistry and materials chemistry. [0003] Traditional methods of amide synthesis are based on the coupling of amines with carboxylic acids, or the activation of carboxylic acids by converting -OH into a good leaving group (eg, acidic chloride, anhydride). However, these methods typically employ stoichiometric coupling agents and additives, resulting in large amounts of toxic chemicals or by-products. Or an oxidation process to synthesize N-pyridi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/07C07C231/10C07C233/25C07C233/15C07C233/58C07C233/65C07C235/56
CPCC07C231/10C07C2601/14C07C2601/02C07C233/07C07C233/25C07C233/15C07C233/58C07C233/65C07C235/56
Inventor 李江胜谢欣芸田晓京刘佳戴嘉颖姜思
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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