Preparation method of N-iodobenzene-N-phenyl amide compound

A technology for phenyl amides and compounds, which is applied in the field of novel preparation of aryl amide compounds, can solve the problems of poor applicability, environmental pollution, dangerous preparation conditions, etc., and achieves the effects of mild reaction conditions, high selectivity and environmental friendliness

Active Publication Date: 2020-09-01
HUBEI UNIV OF TECH
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  • Description
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Problems solved by technology

However, there are certain limitations in the reaction conditions, such as: poor applicability, dangerous preparation conditions, environmental pollution, etc. Traditionally, Cu or Pd is used as a catalyst for this type of reaction, and one or more relatively Expensive metals are used as auxiliary reagents for the reaction, and the reaction conditions will generate a large amount of metal waste while increasing the cost of the reaction
With the strengthening of people's awareness of environmental protection and the current development trend of green, efficient and economical chemical reactions, the reaction conditions of this type of reaction need to be improved.

Method used

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  • Preparation method of N-iodobenzene-N-phenyl amide compound
  • Preparation method of N-iodobenzene-N-phenyl amide compound
  • Preparation method of N-iodobenzene-N-phenyl amide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1, the preparation of N-(4-iodo-3-toluene)-N-phenylacetamide

[0019]

[0020] Add 0.2mmol of acetanilide, 0.3mmol of 2-iodotoluene, 0.3mmol of m-chloroperoxybenzoic acid, 1mL of hexafluoroisopropanol and one No. 5 magnet in sequence, pass the condensed water through the condenser tube from bottom to top, and then close the reactor Put it in an oil bath at 40-80°C and heat it for 2-8 hours, add 15mL of water, extract three times with 10mL of ethyl acetate each time, combine the obtained organic phases, spin dry with a rotary evaporator, and separate and purify the crude product by column chromatography , to obtain 65.3 mg of N-(4-iodobenzene)-N-acetanilide as a yellow solid with a yield of 93%.

[0021] The structure of the product is determined by H NMR and C NMR: 1 H NMR (400MHz, CDCl 3 ): δ2.05(s,3H),2.38(s,3H),6.79(d,J=7.96Hz 2H),7.16(s,1H),7.24(d,J=8.2Hz 2H),7.38(s ,1H),7.76(s,1H); 13 C NMR (100MHz, CDCl 3 ): δ24.3, 28.2, 127.9, 129.6, 139.5, 142...

Embodiment 2

[0022] Embodiment 2, the preparation of N-(4-iodo-3-ethylbenzene)-N-phenylacetamide

[0023]

[0024] Add 0.2mmol of acetanilide, 0.3mmol of 2-ethyl iodobenzene, 0.3mmol of m-chloroperoxybenzoic acid, 1mL of hexafluoroisopropanol and one No. 5 magnet in sequence, pass condensed water through the condenser tube from bottom to top The reactor was placed in a 40-80°C oil bath and heated for 2-8 hours. Add 15mL of water and extract three times with 10mL of ethyl acetate each time. The obtained organic phases were combined and spin-dried by a rotary evaporator. The crude product was subjected to column chromatography After separation and purification, 64.2 mg of N-(4-iodo-3-ethylbenzene)-N-acetanilide was obtained as a yellow solid with a yield of 88%.

[0025] The structure of the product is determined by H NMR and C NMR: 1 H NMR (400MHz, CDCl 3 ): δ1.17(t, J=7.32Hz, 3H) 2.06(s, 3H), 2.68(d, J=6.52Hz, 2H), 6.80(q, J=2.48Hz J=5.88Hz 1H), 7.14 (d, J=2.28Hz 1H), 7.25(d, J=7.72H...

Embodiment 3

[0026] Embodiment 3, the preparation of N-(1,3-dimethyl-2-iodobenzene)-N-phenylacetamide

[0027]

[0028] Add 0.2mmol of acetanilide, 0.3mmol of 1,3-dimethyl-2-iodobenzene, 0.3mmol of m-chloroperoxybenzoic acid, 1mL of hexafluoroisopropanol and one No. After passing the condensed water to the top, place the reactor in an oil bath at 40-80°C and heat for 2-8 hours, add 15mL of water, extract three times with 10mL of ethyl acetate each time, combine the obtained organic phases, and spin dry with a rotary evaporator , the crude product was separated and purified by column chromatography to obtain 45.99 mg of N-(4-iodobenzene)-N-acetanilide as a yellow solid with a yield of 63%.

[0029] The structure of the product is determined by H NMR and C NMR: 1 H NMR (400MHz, CDCl 3 ): δ2.05(s,3H),2.43(s,6H),6.98(s,2H),7.25-7.27(m,3H),7.37(s,2H); 13 C NMR (100MHz, CDCl 3 ): δ23.8, 29.7, 125.1, 126.6, 128.2, 129.7, 142.9, 170.4.

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Abstract

The invention relates to a preparation method of an N-iodobenzene-N-phenyl amide compound, which comprises the following steps: adding substituted acetanilide, substituted iodobenzene, m-chloroperoxybenzoic acid and hexafluoroisopropanol into a reactor, putting the reactor into an oil bath pot at 40-80 DEG C, carrying out reflux condensation, magnetically stirring, and heating to react for 4-10 hours; pouring the obtained reaction liquid into a separating funnel, adding distilled water, extracting for three times by using an organic solvent, carrying out reduced pressure distillation on an organic phase to obtain a crude product, and carrying out column chromatography separation and purification to obtain the N-iodobenzene-N-phenyl amide compound. The method has the advantages of mild reaction conditions, high selectivity, high yield and environmental friendliness. The synthesized N-iodobenzene-N-phenyl amide compound has certain biological activity and can be applied to the fields ofdrug synthesis, pesticide synthesis, paint and dye synthesis and the like.

Description

technical field [0001] The invention relates to a novel preparation method of arylamide compounds, in particular to a preparation method of N-iodobenzene-N-phenylamide compounds. Background technique [0002] Arylamide compounds are important chemical intermediates and products, which are widely used in medicine, pesticides, coatings, dyes and other fields. For example, Quanfloxin is a common antitumor drug; Levofloxacin is a commonly used anti-inflammatory and bactericidal drug; Mifepristone is a hormone regulator; Quinuprisitin is a natural product molecule with anti-inflammatory effects. The universal application of arylamide compounds has aroused great interest of scientific researchers, making the research in this field one of the current research hotspots. [0003] The synthesis method of N-iodobenzene-N-amide compounds is mainly the amination reaction of iodoarenes with arylamides under the catalysis of metal Cu or Pd. However, there are certain limitations in the r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C233/15C07C233/59C07C233/66
CPCC07C231/12C07C233/15C07C233/59C07C233/66
Inventor 张谦杨鹏汪亮余彦葶李栋
Owner HUBEI UNIV OF TECH
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