Application of surface-modified sludge carbon catalyst to carbenoid insertion N-H reaction

A technology of amine compounds and methyl phenylacetate, which is applied in the application field of surface-modified sludge carbon catalysts in the carbene intercalation N-H reaction, to achieve the effects of easy separation and purification, low cost and easy availability of raw materials

Inactive Publication Date: 2018-12-21
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Using surface-modified sludge charcoal to catalyze such reactions, through the formation of metal carbene and...

Method used

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  • Application of surface-modified sludge carbon catalyst to carbenoid insertion N-H reaction
  • Application of surface-modified sludge carbon catalyst to carbenoid insertion N-H reaction
  • Application of surface-modified sludge carbon catalyst to carbenoid insertion N-H reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] Sludge charcoal catalyst preparation: (1) Take a small amount of sludge from municipal domestic sewage plants and dry it at 110°C until the weight remains unchanged; (2) Heat the sludge obtained in (1) in a nitrogen atmosphere to 5°C The heating rate per minute was raised to 600°C, and the calcination time was 6h. After being cooled to 25°C, and mechanically pulverized, a sludge charcoal carrier with high specific surface area and high porosity was obtained. Take 5L of the sludge charcoal obtained in (2), soak it with 5L of perchloric acid with a mass fraction of 30wt.% for 24h, then rinse the soaked sludge charcoal with deionized water until the pH value of the effluent is greater than 6, and then treat the The final sludge charcoal was air-dried at room temperature to obtain a perchloric acid surface-modified sludge charcoal catalyst.

[0031] At room temperature, successively weigh phenyldiazoacetate methyl ester 2a (0.5mmol), aniline 3a (0.65mmol), SW-HC...

Embodiment 2

[0033]

[0034] At room temperature, successively weigh phenyldiazoacetate methyl ester 2a (0.5mmol), p-trifluoromethylaniline 3b (0.65mmol), SW-HClO 4 (100 mg) was added to a 25 mL Schlenk reaction flask under air atmosphere, 5 mL of 1,2-dichloroethane was added, stirred at room temperature for 2 minutes, and reacted in an oil bath at 40° C. for 1 hour. After the reaction, the mixture was cooled to room temperature, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=10:1 ) to obtain the target product 1b (122 mg, yield 79%) as a white solid. The target product was confirmed by NMR and high-resolution mass spectrometry. The sludge charcoal catalyst used in this example is consistent with Example 1.

Embodiment 3

[0036]

[0037] At room temperature, successively weigh phenyldiazoacetate methyl ester 2a (0.5mmol), m-trifluoromethylaniline 3c (0.65mmol), SW-HClO 4 (100 mg) was added to a 25 mL Schlenk reaction flask under air atmosphere, 5 mL of 1,2-dichloroethane was added, stirred at room temperature for 2 minutes, and reacted in an oil bath at 50° C. for 2 hours. After the reaction, the mixture was cooled to room temperature, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=10:1 ), to obtain the target product 1c (100 mg, yield 65%) as a white solid. The target product was confirmed by NMR and high-resolution mass spectrometry. The sludge charcoal catalyst used in this example is consistent with Example 1.

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Abstract

The invention discloses application of a surface-modified sludge carbon catalyst to a carbenoid insertion N-H reaction. An alpha-(phenylamino)methyl ester phenylacetate derivative is generated in onestep from alpha-diazo ester and an amine compound taken as starting raw materials in the presence of a sludge carbon catalyst treated with perchloric acid under a heating condition through formation of metal carbenoid and an N-H insertion reaction. In the method, natural sludge carbon is adopted, and other extra transition metals do not need to loaded, so that the method has the advantages of lowcost, environmental friendliness, ready availability of raw materials, easiness and convenience in operation, mild synthetic reaction condition and high atom utilization rate, gram-grade scale reactions can be realized, recycling of waste is finished, and the requirement on environment-friendly chemistry is met.

Description

technical field [0001] The invention relates to the application of a surface-modified sludge carbon catalyst in carbene intercalation N-H reaction. Using α-diazo esters and amine compounds as starting materials, using perchloric acid-treated sludge carbon catalysts, under heating conditions, through the formation of metal carbene and N-H insertion reactions, one-step generation of α-(phenylamino)benzene Methyl acetate derivatives. [0002] Compared with the reported synthesis method of α-(phenylamino)phenylacetic acid methyl ester derivatives, the present invention sets up a heterogeneous catalytic system, which is convenient for the separation and purification of products, and the raw materials are easy to obtain, easy to operate, and the synthesis reaction conditions are mild , High efficiency, can reach gram-level reaction scale, yield is 31%-86%, and the product has good functional group diversity. The sludge charcoal catalyst adopted in the present invention has abundan...

Claims

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Application Information

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IPC IPC(8): C07C227/08C07C229/36C07D495/04B01J27/06
CPCB01J27/06C07C227/08C07D495/04C07C229/36
Inventor 黄菲易享炎于杨黄和高振贺常虹乔纳森
Owner NANJING UNIV OF TECH
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