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Preparation method of iodobenzene para-amination compound promoted by m-chloroperoxybenzoic acid

A technology of m-chloroperoxybenzoic acid and compounds, which is applied in the field of para-amination reaction of iodobenzene promoted by m-chloroperoxybenzoic acid, can solve problems such as difficult chemical reactions, achieve environmental friendliness, mild reaction conditions, and selective sex high effect

Active Publication Date: 2020-09-11
HUBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when high-valent iodobenzene reacts, a large amount of iodobenzene will be produced with the reaction, so it is difficult to complete the chemical reaction of atom economy

Method used

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  • Preparation method of iodobenzene para-amination compound promoted by m-chloroperoxybenzoic acid
  • Preparation method of iodobenzene para-amination compound promoted by m-chloroperoxybenzoic acid
  • Preparation method of iodobenzene para-amination compound promoted by m-chloroperoxybenzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1, the preparation of N-(4-iodobenzene)-N-phenylacetamide:

[0018]

[0019] Add 0.2mmol of acetanilide, 0.3mmol of 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, and place the reactor in Heat the reaction in an oil bath at 40-80°C 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 by rotary evaporator, and separate and purify the crude product by column chromatography to obtain N-(4-iodophenyl)-N-acetanilide 55.9 mg, a yellow solid, yield 87%.

[0020] The structure of the product is determined by H NMR and C NMR: 1 H NMR (400MHz, CDCl 3 ): δ2.05(s,3H),7.00-7.03.(m,2H),7.24(d,J=7.4Hz 2H),7.39(s,3H),7.65(s,2H); 13 C NMR (100MHz, CDCl 3 ): δ 23.9, 128.1, 129.8, 138.1, 142.7 170.4.

Embodiment 2

[0021] Embodiment 2, the preparation of N-(4-iodobenzene)-N-phenylacrylamide:

[0022]

[0023] Add 0.2mmol N-phenylacrylamide, 0.3mmol iodobenzene, 0.3mmol m-chloroperoxybenzoic acid, 1mL 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, 54.4 mg of N-(4-iodobenzene)-N-acetanilide was obtained as a yellow solid with a yield of 78%.

[0024] H NMR 1 H NMR (400MHz, CDCl 3 ): δ5.65(q, J=8.44Hz, J=1.84Hz, 1H), 6.17(q, J=6.48Hz, J=10.28Hz, 1H), 6.47(q, J=14.88Hz, J=1.88 Hz, 1H), 6.99(d, J=8.64Hz, 2H), 7.19-7.21(m, 2H), 7.31(d, J=6.76Hz, 1H), 7.37-7.41(m, 2H), 7.66(d ,J=8.44Hz,1H) 13 C...

Embodiment 3

[0025] Embodiment 3, the preparation of N-(4-iodobenzene)-N-phenylbutenamide:

[0026]

[0027] Add 0.2mmol N-phenylbutenamide, 0.3mmol iodobenzene, 0.3mmol m-chloroperoxybenzoic acid, 1mL hexafluoroisopropanol and No. 5 magnet in sequence, and pass the condensed water through the condenser tube from bottom to top Put the reactor 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 pass the crude product through the column Chromatographic separation and purification gave 58.1 mg of N-(4-iodobenzene)-N-acetanilide as a yellow solid with a yield of 80%.

[0028] H NMR 1 H NMR (400MHz, CDCl 3 ): δ3.06(d, J=6.68Hz, 2H), 5.00(q, J=15.92Hz, J=1.26Hz, 1H), 5.12(q, J=8.84Hz, J=1.36Hz, 1H), 5.90-6.00(m,1H),7.00-7.03(m,2H),7.23-7.26(m,2H),7.39(s,3H),7.65(d,J=0.36Hz,2H); 13 C NMR (100MHz, CDCl 3 ): δ40.3, 118.2, 128.2, 129.7, 131...

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Abstract

The invention relates to a preparation method of an iodobenzene para-aminated compound promoted by m-chloroperoxybenzoic acid, and the method comprises the following steps: adding substituted acetanilide, iodobenzene, m-chloroperoxybenzoic acid and hexafluoroisopropanol into a reactor, putting the reactor into an oil bath pot at 40-80 DEG C, condensing, refluxing, 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 pressuredistillation on an organic phase to obtain a crude product, and carrying out column chromatography separation and purification to obtain the iodobenzene para-aminated compound. The method is mild in reaction condition, high in selectivity, high in yield and environmentally friendly, and the synthesized aryl amide compound has certain biological activity and can be applied to the fields of medicinesynthesis, pesticide synthesis, paint and dye synthesis and the like.

Description

technical field [0001] The invention relates to a new method for synthesizing arylamide compounds through the para-amination reaction of iodobenzene, in particular to a method for the para-amination reaction of iodobenzene promoted by m-chloroperoxybenzoic acid. Background technique [0002] The system in which hypervalent iodobenzene directly participates in the reaction can complete many reactions that can only be carried out by metal catalysis, not only can directly carry out the aryl amination reaction under metal-free conditions, but also can locate the reaction site. However, when high-valent iodobenzene reacts, a large amount of iodobenzene will be produced with the reaction, so it is difficult to complete the chemical reaction of atom economy. Our research and development uses m-chloroperoxybenzoic acid as the oxidant, and iodobenzene only reacts in a catalytic amount, which can ensure that the reaction is green, efficient, and highly atom-economical. Contents of t...

Claims

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Application Information

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IPC IPC(8): C07C231/08C07C233/15
CPCC07C231/08C07C233/15
Inventor 张谦杨鹏汪亮季慧慧李栋
Owner HUBEI UNIV OF TECH
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