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A method for preparing amides

An amide and ketoxime technology, applied in the field of amide preparation, can solve the problems of equipment corrosion, environmental pollution, low-value ammonium sulfate, etc., and achieve the effects of less by-products, good selectivity and simple treatment

Active Publication Date: 2018-02-06
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the conversion rate of cyclohexanone oxime in the whole reaction is almost 100%, and the selectivity of caprolactam is 99%, the whole reaction not only produces a large amount of low-value ammonium sulfate, but also the catalyzed concentrated sulfuric acid will cause corrosion and environmental pollution to the whole equipment. And other issues

Method used

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  • A method for preparing amides
  • A method for preparing amides
  • A method for preparing amides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In a 50ml three-neck round-bottomed flask, add 0.135g of acetophenone oxime, and connect it with a spherical condenser. On the schlenk, perform pumping and ventilation for 3 times. The system is maintained under an Ar atmosphere, then add 10ml of acetonitrile, stir and heat to 80 ℃. Then add tropone and 8.6ul oxalyl chloride of 10ul, reflux reaction, follow up reaction by liquid chromatography analysis (add a little ethyl acetate to dilute in the sample after sampling): 70% of raw material conversion in the time of 10min, raw material is completely in 20min Conversion, the selectivity of target product acetanilide>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. 1 H NMR (400MHz, CDCl 3 )δ7.90(brs, 1H), 7.49(d, 2H), 7.29(t, 2H), 7.09(t, 1H), 2.14(s, 3H). 13 C NMR (101MHz, CDCl 3 )δ168.90, 138.10, 129.03, 124.39, 120.18, 24.58.

Embodiment 2

[0031] In a 50ml three-neck round bottom flask, add 0.197g of benzophenone oxime, connected with a spherical condenser, on the schlenk, carry out pumping and ventilation for 3 times, and keep the system under Ar atmosphere, then add 10ml of acetonitrile, stir and heat to 80°C. Then add 10ul tropotrienone and 8.6ul oxalyl chloride, reflux reaction, follow the reaction by liquid chromatography analysis (add a little ethyl acetate to dilute the sample after sampling): 70% of raw material conversion in 30min, complete raw material in 1h Conversion, the selectivity of target product benzanilide>98%. After the reaction, the solvent was distilled off under reduced pressure, and pure benzanilide was obtained as a white solid by flash preparative chromatography. 1 H NMR (400MHz, CDCl 3 )δ7.93(s, 1H), 7.85(t, 2H), 7.64(t, 2H), 7.54(t, 1H), 7.47(t, 2H), 7.36(t, 2H), 7.15(t, 1H ). 13 C NMR (101MHz, CDCl 3 )δ165.93, 138.07, 135.14, 131.94, 129.21, 128.90, 127.16, 124.70, 120.39.

Embodiment 3

[0033] In a 50ml three-neck round bottom flask, add 0.135g of acetophenone oxime and 8mg of 1,1-dichlorocycloheptatriene, and connect it with a spherical condenser. On the schlenk, perform air exchange for 3 times, and the system maintains Under N2 atmosphere, then add 10ml of acetonitrile, stir and heat to reflux reaction at 80°C, follow the reaction by liquid chromatography analysis (add a little ethyl acetate to the sample to dilute after sampling): 72% of raw material conversion in 10 min, complete conversion of raw material within 20 min , the selectivity of target product acetanilide>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. 1 H NMR (400MHz, CDCl 3 )δ7.90(brs, 1H), 7.49(d, 2H), 7.29(t, 2H), 7.09(t, 1H), 2.14(s, 3H). 13 CNMR (101MHz, CDCl 3 )δ168.90, 138.10, 129.03, 124.39, 120.18, 24.58.

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Abstract

The invention discloses an amide preparation method, and belongs to the field of organic chemistry. The method is characterized in that amid is generated through a catalytic rearrangement reaction of ketoxime in an organic solvent under the action of 1,1-dichlorocycloheptatriene used as a high-efficiency organic catalyst. Compared with present catalysis systems, the method disclosed in the invention has the obvious advantages of low use amount, mildness, high efficiency, wide sources, simplicity in synthesis, multiple kinds, wide range and no metals. The method also has the characteristics of simple steps, few byproducts and high target product yield.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a method for preparing amides. Background technique [0002] Due to its excellent catalytic effect in catalyzing asymmetric synthesis reactions, organic small molecule catalysts have become a research hotspot in recent years. Compared with transition metal catalysts and enzyme catalysts, organic small molecule catalysts have the advantages of simple structure, easy preparation, no metal ions, mild reaction conditions, cheap and easy-to-obtain raw materials, strong stability and environmental friendliness, but they also have Some drawbacks, the most notable of which is the relatively large amount of catalyst used. This undoubtedly hinders their wider application in the field of organic synthesis and industrial production for those organic small molecule catalysts that are slightly expensive or require multi-step reactions to be synthesized. Therefore, the development...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/10C07C233/07C07C233/65C07D225/02C07D223/10
CPCC07C231/10C07D223/10C07D225/02C07C233/07C07C233/65
Inventor 郭凯刘晶晶李振江徐嘉熙郭天佛欧阳平凯
Owner NANJING TECH UNIV
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