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Method of catalyzing trifluoro-ethylation of aromatic primary amine by ferriporphyrin

A technology of iron porphyrin catalyzing aromatic primary amine trifluoroethyl, aromatic primary amine, applied in chemical instruments and methods, catalytic reaction, physical/chemical process catalyst, etc., can solve the separation of trifluorodiazonium salt, high reaction temperature , poor tolerance of substrate functional groups, etc., to achieve the effect of low cost, simple operation and few reaction steps

Active Publication Date: 2018-12-14
YUANJIANG HUALONG CATALYST TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have the following defects to varying degrees: 1. The reaction temperature is high (250 ° C), and the substrate functional group tolerance is poor; 2. Noble metal catalysts such as metal palladium catalysts are required; 3. Trifluorodiazonium salts need to be separated

Method used

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  • Method of catalyzing trifluoro-ethylation of aromatic primary amine by ferriporphyrin
  • Method of catalyzing trifluoro-ethylation of aromatic primary amine by ferriporphyrin
  • Method of catalyzing trifluoro-ethylation of aromatic primary amine by ferriporphyrin

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Embodiment 1

[0045] Synthesis of 2-methyl-N-(2,2,2-trifluoroethyl)aniline

[0046]Add 2mmol trifluoroethylamine hydrochloride, 1mL water, 34uL acetic acid, 1mL dichloromethane into the reaction tube, cover with a rubber stopper, and fix it on the stirrer. Take 42mg of sodium nitrite in a 1.5mL sample tube, add 1mL of water to the sample tube, shake the sample tube to dissolve the sodium nitrite. Add the dissolved sodium nitrite solution dropwise into the reaction tube with a syringe, and keep stirring for half an hour at room temperature. Dissolve the iron porphyrin (R 2 = R 3 = H, R 1 =Cl, L=Cl) (catalytic amount, 9 / 1000 of the molar amount of primary amine), take 0.24 mmol of 2-methylaniline in a sample tube. After half an hour, the mixed solution in the sample tube was added dropwise into the reaction tube, stirred while adding, and reacted for twelve hours. The reaction solution was cooled to room temperature, filtered to remove some impurities, concentrated and purified by column...

Embodiment 2

[0083] Synthesis of 3-methyl-N-(2,2,2-trifluoroethyl)aniline

[0084] Add 2mmol trifluoroethylamine hydrochloride, 1mL water, 34uL acetic acid, 1mL dichloromethane into the reaction tube, cover with a rubber stopper, and fix it on the stirrer. Take 42mg of sodium nitrite in a 1.5mL sample tube, add 1mL of water to the sample tube, shake the sample tube to dissolve the sodium nitrite. Add the dissolved sodium nitrite solution dropwise into the reaction tube with a syringe, and keep stirring for half an hour at room temperature. Dissolve the iron porphyrin (R 2 = R 3 = H, R 1 =Cl, L=Cl) (catalytic amount, 9 / 1000 of the molar amount of primary amine), take 0.24 mmol of 3-methylaniline in a sample tube. After half an hour, the mixed solution in the sample tube was added dropwise into the reaction tube, stirred while adding, and reacted for twelve hours. The reaction solution was cooled to room temperature, filtered to remove some impurities, concentrated and purified by colum...

Embodiment 3

[0089] Synthesis of 4-methyl-N-(2,2,2-trifluoroethyl)aniline

[0090] Add 2mmol trifluoroethylamine hydrochloride, 1mL water, 34uL acetic acid, 1mL dichloromethane into the reaction tube, cover with a rubber stopper, and fix it on the stirrer. Take 42mg of sodium nitrite in a 1.5mL sample tube, add 1mL of water to the sample tube, shake the sample tube to dissolve the sodium nitrite. Add the dissolved sodium nitrite solution dropwise into the reaction tube with a syringe, and keep stirring for half an hour at room temperature. Dissolve the iron porphyrin (R 2 =R 3 =CH 3 , R 1 =Cl, L=Cl) (catalytic amount, 9 / 1000 of the molar amount of primary amine), take 0.24 mmol of 3-methylaniline in a sample tube. After half an hour, the mixed solution in the sample tube was added dropwise into the reaction tube, stirred while adding, and reacted for twelve hours. The reaction solution was cooled to room temperature, filtered to remove some impurities, concentrated and purified by co...

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Abstract

The invention provides a method of catalyzing trifluoro-ethylation of aromatic primary amine by ferriporphyrin. The method comprises the following steps: adding trifluoroethylamine salt and nitrite toa diazo-reaction first and then adding aromatic primary amine and a ferriporphyrin catalyst for a trifluoro-ethylation reaction to obtain a trifluoro-ethylated aromatic primary amine compound in an acidic solution system. The reactions of the method are carried out at room temperature, the reaction condition is mild, and an intermediate product is not separated through a one-pot reaction. The method is few in reaction step, simple to operate, wide in application range of primers, wide in source of raw materials and high in yield of reaction products.

Description

technical field [0001] The invention relates to a method for trifluoroethylation of primary aromatic amines catalyzed by iron porphyrin, in particular to a method for diazotizing trifluoroethylamine and then substituting with primary aromatic amines to generate trifluoroethylated primary aromatic amine compounds; The field of organic intermediate synthesis. Background technique [0002] N-trifluoroethylated aromatic amines are a class of biologically active chemicals widely used in the fields of medicine and agricultural chemistry. The construction of N-trifluoroethylated aromatic amines has always been an interesting research direction, and a large number of literatures have reported the synthesis of N-trifluoroethylated aromatic amines. At present, there are mainly two methods to construct N-trifluoroethylated aromatic amines (Haghighi, F.; Panahi, F.; Golbon, M.H, Khalafinezhad. Chem. Commun. 2017, 53, 12650-1265), one is to use Aryl halides are coupled with 2,2,2-trifl...

Claims

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Application Information

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IPC IPC(8): C07C211/48C07C209/22B01J31/22B01J31/28
CPCB01J31/22B01J31/2217B01J31/28B01J2231/4283B01J2531/025B01J2531/842C07C209/22C07C211/48
Inventor 刘强许桂铭郭灿城
Owner YUANJIANG HUALONG CATALYST TECH
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