Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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

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 Tolerance is poor and other problems, to achieve the effect of simple operation, low cost, few reaction steps

Active Publication Date: 2018-12-14
YUANJIANG HUALONG CATALYST TECH
View PDF4 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method of catalyzing trifluoro-ethylation of aromatic secondary amine by ferriporphyrin
  • Method of catalyzing trifluoro-ethylation of aromatic secondary amine by ferriporphyrin
  • Method of catalyzing trifluoro-ethylation of aromatic secondary amine by ferriporphyrin

Examples

Experimental program
Comparison scheme
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 of reaction. The reaction solution was cooled to room temperature, filtered to remove some impurities, concentra...

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 re...

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
boiling pointaaaaaaaaaa
Login to View More

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 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...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com