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A method for trifluoroethylation of aromatic secondary amines catalyzed by iron porphyrin

A technology of iron porphyrin catalyzing aromatic secondary amine trifluoroethyl, aromatic secondary amine, applied in chemical instruments and methods, catalytic reaction, physical/chemical process catalyst, etc., can solve the problem of high reaction temperature, inapplicability, substrate functional group Poor tolerance and other problems, to achieve the effect of simple operation, low cost, and few reaction steps

Active Publication Date: 2021-01-15
YUANJIANG HUALONG CATALYST TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods all have the following defects in varying degrees: 1. The reaction temperature is high (250°C), and the substrate functional group tolerance is poor; noble metal catalysts such as metal palladium catalysts are needed; trifluorodiazonium salts need to be separated; only applicable to primary amines , not applicable to secondary amines

Method used

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  • A method for trifluoroethylation of aromatic secondary amines catalyzed by iron porphyrin
  • A method for trifluoroethylation of aromatic secondary amines catalyzed by iron porphyrin
  • A method for trifluoroethylation of aromatic secondary amines catalyzed by iron porphyrin

Examples

Experimental program
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Effect test

Embodiment 1

[0047] Synthesis of N-methyl-N-(2,2,2-trifluoroethyl)aniline

[0048] Add 2mmol trifluoroethylamine hydrochloride, 1mL water, 34uL acetic acid, 1mL dichloroethane 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 TPPFeCl (catalytic amount, 9 / 1000 of the molar amount of secondary amine) with 1 mL of dichloroethane, and take 0.24 mmol of N-methylaniline in the sample tube. Half an hour later, the mixed solution in the sample tube was added dropwise into the reaction tube, stirred while adding, and the temperature was raised to 80°C for 12 hours. The reaction solution was cooled to room temperature, filtered to remove some impurities, concentrated and puri...

Embodiment 2

[0086] Synthesis of 4-methoxy-N-methyl-N-(2,2,2-trifluoroethyl)aniline

[0087] Add 2mmol trifluoroethylamine hydrochloride, 1mL water, 34uL acetic acid, 1mL dichloroethane 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 secondary amine), take 0.24 mmol of 4-methoxy-N-methylaniline in a sample tube. Half an hour later, the mixed solution in the sample tube was added dropwise into the reaction tube, stirred while adding, and the temperature was raised to 80°C for 12 hours of reaction. The reaction solution was cooled to room temperature, filtered to rem...

Embodiment 3

[0092] Synthesis of N,4-Dimethyl-N-(2,2,2-trifluoroethyl)aniline

[0093] Add 2mmol trifluoroethylamine hydrochloride, 1mL water, 34uL acetic acid, 1mL dichloroethane 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 1 = H, R 2 =R 3 = CF 3 , L=OAc) (catalytic amount, 9 / 1000 of the molar amount of secondary amine), take 0.24 mmol of N,4-dimethylaniline in a sample tube. Half an hour later, the mixed solution in the sample tube was added dropwise into the reaction tube, stirred while adding, and the temperature was raised to 80°C for 12 hours of reaction. The reaction solution was cooled to room temperature, filtered to remove so...

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Abstract

The invention provides a method of catalyzing trifluoro-ethylation of aromatic secondary amine by ferriporphyrin. The method comprises the following steps: adding trifluoroethylamine salt and nitriteto a diazo-reaction first and then adding aromatic primary amine and a ferriporphyrin catalyst for a trifluoro-ethylation reaction to obtain a trifluoro-ethylated aromatic secondary amine compound inan acidic solution system. The reactions of the method are carried out at room temperature, and 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 secondary aromatic amines catalyzed by iron porphyrin, in particular to a method for diazotizing trifluoroethylamine and then substituting with secondary aromatic amines to generate trifluoroethylated secondary 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 two main 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-t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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