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Preparation method of formamide compound

A technology for amine compounds and formamides is applied in the field of preparation of formamide compounds, and achieves the effects of good catalyst repeatability, simple operation and post-processing, and high product yield

Active Publication Date: 2021-10-22
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in these methods, there have been no reports on the method of nanoporous palladium catalysts to catalyze carbon dioxide to construct new C–N bonds into formamides.

Method used

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  • Preparation method of formamide compound
  • Preparation method of formamide compound
  • Preparation method of formamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the synthesis of N-methylformanilide

[0036] In a 20mL autoclave, add nanoporous palladium catalyst PdNPore-1 (2.7mg, 0.025mmol), N-methylaniline (53.5mg, 0.5mmol), phenylsilane (216.4mg, 2mmol), acetonitrile (2mL ), deionized water (10 μL) and carbon dioxide (1.0 MPa), placed on a magnetic stirrer at 60 ° C for 20 h, column chromatography (silica gel, 200-300 mesh; developer, petroleum ether, ethyl acetate = 2: 1) Obtain 53.7 mg of N-methylformanilide, yield 85%

[0037]

[0038] yellow oily liquid; 1 H NMR (CDCl 3 ,400MHz)δ8.46(s,1H),7.42-7.37(m,2H),7.28-7.24(m,1H),7.16(d,J=8.0Hz,2H),3.30(s,3H); 13 C NMR (CDCl 3 ,100MHz) δ162.3, 142.2, 129.6, 126.4, 122.3, 32.0.

Embodiment 2

[0039] Embodiment 2: the synthesis of N-methyl-4-methoxyformanilide

[0040] In a 20mL autoclave, add nanoporous palladium catalyst PdNPore-1 (2.7mg, 0.025mmol), N-methyl-4-methoxyaniline (68.5mg, 0.5mmol), phenylsilane (216.4mg, 2mmol), acetonitrile (2mL), deionized water (10μL) and carbon dioxide (2.0MPa), placed on a magnetic stirrer at 70 ° C for 24h, column chromatography (silica gel, 200-300 mesh; developer, petroleum ether, Ethyl acetate = 2:1) to obtain 75.1 mg of N-methyl-4-methoxyformanilide with a yield of 91%.

[0041]

[0042] yellow oily liquid; 1 H NMR (CDCl 3 ,400MHz)δ8.34(s,1H),7.10(d,J=8.0Hz,2H),6.93(d,J=8.0Hz,2H),3.83(s,3H),3.27(s,3H); 13 C NMR (CDCl 3,100MHz)δ162.5,158.3,135.3,124.7,114.8,55.5,32.7.

Embodiment 3

[0043] Embodiment 3: the synthesis of N-allyl formanilide

[0044] In a 20mL autoclave, add nanoporous palladium catalyst PdNPore-1 (2.7mg, 0.025mmol), N-allylaniline (66.5mg, 0.5mmol), phenylsilane (270.5mg, 2.5mmol), acetonitrile (2mL), deionized water (10μL) and carbon dioxide (1.0MPa), placed on a magnetic stirrer at 70 ° C for 24h, column chromatography (silica gel, 200-300 mesh; developer, petroleum ether, ethyl acetate = 2:1) to obtain 64.5mg of N-allylformanilide, yield 80%

[0045]

[0046] Yellow oily liquid. 1 H NMR (CDCl 3 ,400MHz)δ8.40(s,1H),7.32-7.27(m,2H),7.20-7.17(m,1H),7.10(d,J=8.0Hz,2H),5.81-5.71(m,1H) ,5.12-5.07(m,2H),4.33(d,J=8.0Hz,2H); 13 C NMR (CDCl 3 ,100MHz)δ162.0,141.2,132.5,130.0,126.7,123.5,117.6,47.8.

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Abstract

The invention belongs to the technical field of activation and conversion of CO2 and related chemistry, and provides a preparation method of a formamide compound. The method is characterized in that: carbon dioxide, an amine compound and phenylsilane are used as raw materials, and the formamide compound is synthesized under the action of a nano-porous palladium catalyst. The invention mainly provides a novel simple catalytic system, the formamide compound is synthesized by using CO2 as a C1 source, and the catalytic system has the advantages of mild reaction conditions, simple experimental operation, good functional group compatibility and the like. The carbon dioxide is a renewable C1 source which is rich in reserves, low in price and easy to obtain, so that the formamide compound has relatively high application value and social and economic benefits.

Description

technical field [0001] The invention belongs to CO 2 Activation conversion and related chemical technology field, involving a CO 2 as C 1 The preparation method of the carboxamide compound of source. Background technique [0002] Carbon dioxide is an abundant, cheap and renewable C 1 The research on its catalytic conversion into high value-added fine chemicals has attracted widespread attention. In the past few decades, a lot of carbon dioxide fixation and conversion methods have been reported [see: (a) Katagiri, T.; Amao, Y. Green Chem. 2020, 22, 6682. (b) He, M. ; Sun, Y.; Han, B.. Angew. Chem. Int. Ed.. 2013, 57, 9620.]. Among these methods, the method of catalyzing the conversion of carbon dioxide to form new C–N bonds is an effective method for the synthesis of high value-added fine chemicals because of its high selectivity, good functional group compatibility, and mild reaction conditions. [See: (a) Hu, X.; Wu, Y. Chem. Commun. 2017, 53, 8046. (b) Hasegawa, J.; E...

Claims

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Application Information

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IPC IPC(8): C07B43/06C07C231/10C07C233/03C07C233/25C07C233/15C07D215/40B01J23/44B01J23/96B01J35/10
CPCC07B43/06C07C231/10C07D215/40B01J23/44B01J23/96B01J35/393B01J35/643B01J35/647C07C233/03C07C233/25C07C233/15Y02P20/584
Inventor 冯秀娟王继虓包明
Owner DALIAN UNIV OF TECH
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