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Preparation method of amide

A technology of amides and heterocycloalkanediones, which is applied in the preparation of lactams, carboxylic acid amides, and organic compounds, can solve the problems of reporting diazacycloalkanediones and other problems, and achieve low raw material prices , mild reaction conditions, and good industrial application prospects

Active Publication Date: 2017-08-04
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

Although there are reports (H.Ulrich et al., J.Org.Chem., 1965,30,2781-2783 on the synthesis of 1,3-diazacycloalkanedione derivatives; G.Zinner et al., Chem.Ber. , 1970,103,766-776), but there is no relevant report using 1,3-diazacycloalkanedione derivatives as catalysts, let alone 1,3-diazacycloalkanedione derivatives as Catalysts for Beckmann Rearrangement Reaction

Method used

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  • Preparation method of amide
  • Preparation method of amide
  • Preparation method of amide

Examples

Experimental program
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Embodiment 1

[0034] In a sealed Schlenk tube, add 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione (7) (33.33 mg, 0.1 mmol), acetophenone oxime (0.135 g, 1 mmol) was dissolved in 10 mL of acetonitrile, stirred and heated to 80° C. under the protection of Ar, the raw material was completely converted in 20 min, and the selectivity of the target product acetanilide was >99%. After the reaction, the solvent was distilled off under reduced pressure, and pure acetanilide was obtained as a white solid by flash preparative chromatography with a yield of 98%. 1 H NMR (400MHz, CDCl 3 )δ8.22(s,1H),7.43(d,J=7.9Hz,2H),7.19(t,J=7.8Hz,2H),7.00(d,J=7.4Hz,1H),2.04(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ169.20, 138.14, 128.93, 124.32, 120.27, 24.41.

Embodiment 2

[0036] In a sealed Schlenk tube, add 2,2-dichloro-1,3-diisopropylimidazolidine-4,5-dione (1) (25.31 mg, 0.1 mmol), acetophenone oxime (0.135 g , 1 mmol) was dissolved in 10 mL of acetonitrile, stirred and heated to 80° C. under the protection of Ar, the raw material was completely converted in 20 min, and the selectivity of the target product acetanilide was 97%. After the reaction, the solvent was distilled off under reduced pressure, and pure acetanilide was obtained as a white solid by flash preparative chromatography with a yield of 95%. 1 H NMR (400MHz, CDCl 3 )δ8.22(s,1H),7.43(d,J=7.9Hz,2H),7.19(t,J=7.8Hz,2H),7.00(d,J=7.4Hz,1H),2.04(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ169.20, 138.14, 128.93, 124.32, 120.27, 24.41.

Embodiment 3

[0038] In a sealed Schlenk tube, add 2,2-dibromo-1,3-di-tert-butylimidazolidine-4,5-dione (2) (34.20 mg, 0.1 mmol), acetophenone oxime (0.135 g , 1 mmol) was dissolved in 10 mL of acetonitrile, stirred and heated to 80° C. under the protection of Ar, the raw material was completely converted in 20 min, and the selectivity of the target product acetanilide was 98%. After the reaction, the solvent was distilled off under reduced pressure, and pure acetanilide was obtained as a white solid by flash preparative chromatography with a yield of 96%. 1 H NMR (400MHz, CDCl 3 )δ8.22(s,1H), 7.43(d,J=7.9Hz,2H),7.19(t,J=7.8Hz,2H),7.00(d,J=7.4Hz,1H),2.04(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ169.20, 138.14, 128.93, 124.32, 120.27, 24.41.

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Abstract

The invention discloses a preparation method of amide, and belongs to the field of organic chemistry. A 1,3-diazacyclothiazolidinedione derivative is used as a novel organic small molecule catalyst to catalyze ketoxime rearrangement reaction, the amide generation speed is high, in most of reactions, within 10-30 minutes, selectivity can reach 98%, and the separating yield can be 95% or above. The preparation method is gentle in reaction conditions, and can be carried out under normal pressure and at the temperature from the room temperature to the temperature of 100 DEG C, instruments and equipment cannot be corroded, environmental pollution cannot be caused, energy is saved, and the industrial application prospect is good. The preparation method of amide is an efficient and environmentally friendly amide preparation method with simple and convenient synthesis steps.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a method for catalytically preparing amides by using 1,3-diazacycloalkanedione derivatives. Background technique [0002] The Beckmann rearrangement reaction discovered in 1886 is an important method to directly convert ketoxime into amides. It is an atom-economical reaction and has important industrial applications. It has been used on a large scale for caprolactam (nylon-6 monomer), Synthesis and production of laurolactam (nylon-12 monomer) and the drug paracetamol. Traditionally, this reaction is carried out under strong acid catalysis and high temperature, which leads to the formation of more by-products and increases the cost of energy consumption. Taking caprolactam as an example, it is mainly used to produce nylon-6 fiber and nylon-6 engineering plastics. The main process for producing caprolactam currently used in industry is to use oleum as a catalyst and so...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/10C07C233/07C07C233/25C07C233/15C07C233/65C07D201/04C07D225/02
CPCC07C231/10C07D201/04C07D225/02C07C233/07C07C233/25C07C233/15C07C233/65
Inventor 郭凯高宇李振江刘晶晶郭天佛
Owner NANJING UNIV OF TECH
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