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Method for catalyzing and synthesizing asymmetric azoxybenzene compound

A technology for azobenzene oxide and compounds, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve the problem of few synthetic methods and difficult separation of asymmetric azobenzene , difficult to prepare and other problems, to achieve good research value and application potential, good product yield effect

Active Publication Date: 2017-11-17
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few synthetic methods of asymmetric azobenzene, and it is not easy to separate, thus limiting the scope of application of this method
2), the product obtained through the coupling reaction of nitrosobenzene compound and aromatic hydroxylamine, aromatic hydroxylamine has poor stability and is not easy to prepare, making this method unable to be widely used
4), through the condensation of ArN(MgBr)2 with its nitrobenzene, however, the amino Grignard reagent is very unstable

Method used

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  • Method for catalyzing and synthesizing asymmetric azoxybenzene compound
  • Method for catalyzing and synthesizing asymmetric azoxybenzene compound
  • Method for catalyzing and synthesizing asymmetric azoxybenzene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: 1-phenyl-2-(4-chlorophenyl) azo oxide

[0031]

[0032] Add 4-chloroaniline (127.5mg, 1.0mmol), nitrosobenzene (107.0mg, 1.0mmol), CuCl (3.0mg, 3mol%), pyridine (20μl, 0.25mmol), toluene to a 100ml reaction tube in sequence (2ml). Then, fill the reaction tube with O 2 (About 1bar). Put the reaction mixture in an oil bath at 65°C and stir for 24 hours, then take it out and cool it to room temperature. Transfer the reaction stock solution, add an appropriate amount of ethyl acetate to wash, mix the stock solution with the washing solution, concentrate under reduced pressure and absorb on silica gel powder. Perform silica gel column chromatography directly, use a mixture of petroleum ether and ethyl acetate in a volume ratio of 100:1 as the eluent, and use column chromatography to obtain 1-phenyl-2-(4-chlorophenyl) oxidation Azo, the yield is 80%.

[0033] Use NMR to confirm that the structure data is

[0034] 1 H NMR(500MHz, CDCl 3 , TMS): δ8.30-8.27(m,2H), 8.17-8...

Embodiment 2

[0035] Example 2: 1-Phenyl-2-(4-methylphenyl) azo oxide

[0036]

[0037] Add 4-methylaniline (107.0mg, 1.0mmol), nitrosobenzene (107.0mg, 1.0mmol), CuCl (3.0mg, 3mol%), pyridine (20μl, 0.25mmol) to a 100ml reaction tube in sequence, Toluene (2ml). Then, fill the reaction tube with O 2 (About 1bar). Put the reaction mixture in an oil bath at 65°C and stir for 24 hours, then take it out and cool it to room temperature. Transfer the reaction stock solution, add an appropriate amount of ethyl acetate to wash, mix the stock solution with the washing solution, concentrate under reduced pressure and absorb on silica gel powder. Perform silica gel column chromatography directly, use a mixture of petroleum ether and ethyl acetate in a volume ratio of 100:1 as the eluent, and use column chromatography to obtain 1-phenyl-2-(4-methylphenyl). Azo oxide, the yield is 91%.

[0038] Confirm the structure data by NMR:

[0039] 1 H NMR(500MHz, CDCl 3 ,TMS): δ8.30(d,J=5Hz,2H), 8.14(d,J=5Hz,2H),7.5...

Embodiment 3

[0040] Example 3: 1-Phenyl-2-(4-methoxyphenyl) azo oxide

[0041]

[0042] Add 4-methoxyaniline (127.0mg, 1.0mmol), nitrosobenzene (107mg, 1.0mmol), CuCl (3mg, 3mol%), pyridine (20μl, 0.25mmol), and toluene into a 100ml reaction tube. (2ml). Then, fill the reaction tube with O 2 (About 1bar). Put the reaction mixture in an oil bath at 65°C and stir for 24 hours, then take it out and cool it to room temperature. Transfer the reaction stock solution, add an appropriate amount of ethyl acetate to wash, mix the stock solution with the washing solution, concentrate under reduced pressure and absorb on silica gel powder. Perform silica gel column chromatography directly, use a mixture of petroleum ether and ethyl acetate with a volume ratio of 100:1 as the eluent, and use column chromatography to obtain 1-phenyl-2-(4-methoxyphenyl) ) Azo oxide, the yield is 80%.

[0043] Confirm the structure data by NMR:

[0044] 1 H NMR(500MHz, CDCl 3 ,TMS): δ8.33(d,J=10Hz,2H), 8.29(d,J=10Hz,2H), 7.5...

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PUM

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Abstract

The invention relates to a method for catalyzing and synthesizing an asymmetric azoxybenzene compound. The method includes the steps that in organic solvent and in the atmosphere of oxygen, a compound catalyzing system composed of CuC1 and aids is used for a catalytic-dehydrogenation condensation reaction. With aromatic amine and nitrosobenzene being raw materials, under conditions of mildness and oxygen, the asymmetric azoxybenzene compound which is widely applied is realized through efficient and selective synthesis. Common CuC1 easy to obtain is used as a catalyst, the raw materials used for synthesis are also easy to obtain, and conditions needed for the reaction are simple, mild and easy to operate. Compared with the prior art, the method has higher actual application value, is environmentally friendly, and can be sustainably applied and popularized.

Description

Technical field [0001] The invention relates to a method for synthesizing azobenzene oxide, in particular to a method for synthesizing an asymmetric azobenzene oxide compound by using CuCl to catalyze the synthesis. Background technique [0002] Azobenzene oxide compounds are important intermediates in industrial production and are widely used in the synthesis of dyes, pesticides, medicines, and photosensitive materials; because of their liquid crystal properties, azobenzene oxide compounds are key materials for electronic equipment; Nitrobenzene compounds are also important precursors of Wallach reaction. [0003] The traditional methods for synthesizing azobenzene oxide mainly include reduction of aromatic nitro compounds and aromatic amine oxidation. [0004] The aromatic amine oxidation process often uses stoichiometric amounts of heavy metal salts such as lead salt, mercury salt, manganese salt, ferrate, diazonium salt, peroxyacetic acid, and environmentally unfriendly oxidants...

Claims

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Application Information

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IPC IPC(8): C07C291/08B01J31/30
CPCC07C291/08B01J31/30
Inventor 王舜余小春任程金辉乐刘爱丽董小妹
Owner WENZHOU UNIVERSITY
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