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

Method for green synthesis of 1,2-diamine compound under catalysis of visible light

A technology for green synthesis and aldehyde compounds, which is applied in the preparation of organic compounds, chemical instruments and methods, and preparation of aminohydroxy compounds, etc., can solve the problems of unobtainable raw materials, high requirements for reaction temperature and pressure, and long reaction time, etc. Achieving the effect of good yield, mild reaction conditions and easy operation

Pending Publication Date: 2020-06-16
HANGZHOU NORMAL UNIVERSITY
View PDF4 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The direct diamination method of the above patents has high requirements on reaction temperature and pressure, and the obtained products are mostly complex mixtures.
The reaction time of indirect diamination method is relatively long, and the raw materials are not easy to obtain

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 for green synthesis of 1,2-diamine compound under catalysis of visible light
  • Method for green synthesis of 1,2-diamine compound under catalysis of visible light
  • Method for green synthesis of 1,2-diamine compound under catalysis of visible light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] (1) Add 90.4 mg N-phenylglycine, 24.7 mg p-methoxyaniline, 2.6 mg photocatalyst {Ir[dF(CF 3 )ppy] 2 bpy}PF 6 , 2 mL 0.1M N , N - Dimethylacetamide, 21.2 mg benzaldehyde, the ratio of benzaldehyde: p-methoxyaniline: N-phenylglycine: photocatalyst is 1:1:3:0.01.

[0076] (2) The Schlenk tube obtained in step (1) is pumped and ventilated three times to ensure that there is no water and oxygen in the reaction tube before sealing it.

[0077] (3) Place the Schlenk tube obtained in step (2) under the irradiation of a Blue LED with a lamp source of 10W and a lambda of 455 nm, and carry out stirring reaction at room temperature for 2 hours. The distance between the Blue LED lamp and the Schlenk tube is 3cm. When TLC detects that the aldehyde compound disappears, the reaction is terminated, and the developer ratio of the TLC detection reaction is PE:EA=10:1.

[0078] (4) Add 15 mL of water to the Schlenk tube obtained in step (3) to quench the reaction, transfer to a separa...

Embodiment 2

[0082] (1) Add 90.4 mg N-phenylglycine, 24.7 mg p-methoxyaniline, 2.6 mg photocatalyst {Ir[dF(CF 3 )ppy] 2 bpy}PF 6 , 2 mL N , N -Dimethylacetamide, 27.2 mg p-methoxybenzaldehyde, the ratio of p-methoxybenzaldehyde: p-methoxyaniline: N-phenylglycine: photocatalyst is 1:1:3:0.01.

[0083] (2) The Schlenk tube obtained in step (1) is pumped and ventilated three times to ensure that there is no water and oxygen in the reaction tube before sealing it.

[0084] (3) Place the Schlenk tube obtained in step (2) under the irradiation of a Blue LED with a lamp source of 10W and a lambda of 455 nm, and carry out stirring reaction at room temperature for 2 hours. The distance between the Blue LED lamp and the Schlenk tube is 3cm. When TLC detects that the aldehyde compound disappears, the reaction is terminated, and the proportioning of the developer during the TLC detection reaction is PE:EA=10:1.

[0085] (4) Add 15 mL of water to the Schlenk tube obtained in step (3) to quench the...

Embodiment 3

[0087] (1) Add 90.4 mg N-phenylglycine, 24.7 mg p-methoxyaniline, 2.6 mg photocatalyst {Ir[dF(CF 3 )ppy] 2 bpy}PF 6 , 2 mL N , N -Dimethylacetamide, 24.1 mg p-tolualdehyde, the ratio of p-tolualdehyde: p-methoxyaniline: N-phenylglycine: photocatalyst is 1:1:3:0.01.

[0088] (2) The Schlenk tube obtained in step (1) is pumped and ventilated three times to ensure that there is no water and oxygen in the reaction tube before sealing it.

[0089] (3) Place the Schlenk tube obtained in step (2) under the irradiation of a Blue LED with a lamp source of 10W and a lambda of 455 nm, and carry out stirring reaction at room temperature for 2 hours. The distance between the Blue LED lamp and the Schlenk tube is 3cm. When TLC detects that the aldehyde compound disappears, the reaction is terminated, and the proportioning of the developer during the TLC detection reaction is PE:EA=10:1.

[0090] (4) Add 15 mL of water to the Schlenk tube obtained in step (3) to quench the reaction, tra...

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

No PUM Login to View More

Abstract

The invention discloses a method for green synthesis of a 1,2-diamine compound through visible light catalysis, and belongs to the technical field of organic synthesis. The method comprises the following steps: (1) adding N-phenylglycine or (4-fluorophenyl) glycine, a photocatalyst, an aldehyde compound or an imine compound, an arylamine compound and a solvent into a dry Schlenk tube; (2) sealingafter three times of air suction and exchange treatment; (3) carrying out stirring reaction under the irradiation of a Blue LED, and ending the reaction when TLC detects that the aldehyde compound disappears; and (4) adding water to quench, extracting with ethyl acetate, collecting an organic phase, drying with anhydrous sodium sulfate, filtering, adding silica gel, concentrating under reduced pressure, and purifying by column chromatography to obtain the diamine compound. Compared with the prior art, the method is simple in synthetic route, easily available in raw materials, simple and convenient to operate, environment-friendly, mild in reaction condition, good in reaction condition controllability and wide in substrate application range, and the preparation of the compound can realize an amplification reaction of gram level or above.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for green synthesis of 1,2-diamine compounds catalyzed by visible light. Background technique [0002] 1,2-diamine compounds, the chemical formula is , The 1,2-diamine compound contains two amino groups, and the N atom of the amino group has a lone pair of electrons. It is easy to coordinate with metal ions to obtain a coordination compound with a variable structure, which widely exists in biologically active drug molecules. For example, 1,2-diaminoplatinum compounds are widely used in antidepressant, hypertension, psychosis and anticancer and antitumor drugs. In addition, the two amino groups of diamine make the corresponding product have excellent adhesion to metal, textile, plastic and mineral surfaces, and can be used as anti-corrosion agent, pigment wetting agent, mineral flotation agent, anti-stripping agent, Petroleum additives, adhesives ...

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
IPC IPC(8): C07C213/02C07C217/84C07C209/60C07C211/53C07D307/52C07D333/20C07D209/08C07D277/82
CPCC07C213/02C07C209/60C07D307/52C07D333/20C07D209/08C07D277/82C07C217/84C07C211/53
Inventor 曾晓飞钟国富潘舒蕾
Owner HANGZHOU NORMAL UNIVERSITY
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