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Method for photocatalytic synthesis of N-alkylphthalimide

A technology of alkyl phthalimide and alkenyl phthalimide is applied in the field of photocatalytic synthesis of N-alkyl phthalimide, which can solve the problem of poor versatility and universality , many by-products, low reaction efficiency and other problems, to achieve the effect of high promotion value and commercial value, less by-products, high reaction efficiency

Pending Publication Date: 2022-06-28
NINGBO UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved in the present invention is to provide a method for photocatalytically synthesizing N-alkylphthalimides to solve the problems of low reaction efficiency, many by-products, and poor versatility and universality in conventional reactions. question

Method used

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  • Method for photocatalytic synthesis of N-alkylphthalimide
  • Method for photocatalytic synthesis of N-alkylphthalimide
  • Method for photocatalytic synthesis of N-alkylphthalimide

Examples

Experimental program
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Effect test

Embodiment 1

[0039] S1: Put the magneton into the reaction tube, add Ir[dF(CF 3 )ppy] 2 (dtbbpy)PF 6 (4.5 mg, 0.004 mmol, 0.02 equiv), 2-(N-phthalimide) ethyl acrylate (49.0 mg, 0.2 mmol, 1.0 equiv); put the reaction tube into the glove box, in the glove box Weigh chloropropyl bis(catechol) silicate-18-crown-6-potassium (249.8 mg, 0.4 mmol, 2.0 equiv);

[0040] S2: The reaction tube was plugged with a rubber stopper and taken out, dry dimethyl sulfoxide (6 mL) was added under nitrogen, and the rubber stopper was tightly sealed with a sealing film. The reaction tube was irradiated under a 9W blue LED lamp, and after stirring and reacting at room temperature for 24 hours, the light reaction was stopped, 6 mL of water was added to the reaction solution, and ethyl acetate (4×10 mL) was used for extraction;

[0041] S3: the organic phases were combined and washed with 5 mL of saturated brine, the organic phase was dried with anhydrous sodium sulfate and filtered, the filtrate was rotary evap...

Embodiment 2

[0046] S1: Put the magneton into the reaction tube, add Ir[dF(CF 3 )ppy] 2 (dtbbpy)PF 6 (4.5 mg, 0.004 mmol, 0.02 equiv), 2-(N-phthalimide) ethyl acrylate (49.0 mg, 0.2 mmol, 1.0 equiv); put the reaction tube into the glove box, in the glove box Weigh cyclohexyl bis(catechol) silicate-18-crown ether-6-potassium (252.0 mg, 0.4 mmol, 2.0 equiv);

[0047] S2: The reaction tube was plugged with a rubber stopper and taken out, dry dimethyl sulfoxide (6 mL) was added under nitrogen, and the rubber stopper was tightly sealed with a sealing film. The reaction tube was irradiated under a 9W blue LED lamp, and after stirring and reacting at room temperature for 24 hours, the light reaction was stopped, 6 mL of water was added to the reaction solution, and ethyl acetate (4×10 mL) was used for extraction;

[0048] S3: the organic phase was combined and washed with 5 mL of saturated brine, the organic phase was dried with anhydrous sodium sulfate and filtered, the filtrate was rotary ev...

Embodiment 3

[0053] S1: Put the magneton into the reaction tube, add Ir[dF(CF 3 )ppy] 2 (dtbbpy)PF 6 (4.5 mg, 0.004 mmol, 0.02 equiv), 1-(N-phthalimide) styrene (49.0 mg, 0.2 mmol, 1.0 equiv); put the reaction tube into the glove box, in the glove box Weigh ethyl bis(catechol) silicate-18-crown ether-6-potassium (230.4 mg, 0.4 mmol, 2.0 equiv);

[0054] S2: The reaction tube was plugged with a rubber stopper and taken out, dry dimethyl sulfoxide (6 mL) was added under nitrogen, and the rubber stopper was tightly sealed with a sealing film. The reaction tube was irradiated under a 9W blue LED lamp, and after stirring and reacting at room temperature for 24 hours, the light reaction was stopped, 6 mL of water was added to the reaction solution, and ethyl acetate (4×10 mL) was used for extraction;

[0055] S3: the organic phases were combined and washed with 5 mL of saturated brine, the organic phase was dried with anhydrous sodium sulfate and filtered, the filtrate was rotary evaporated t...

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Abstract

The invention provides a method for synthesizing N-alkyl phthalimide through photocatalysis, which comprises the following steps: S1, adding N-alkenyl phthalimide and a photosensitizer Ir [dF (CF3) ppy] 2 (dtbbpy) PF6 into a reaction tube with a stirrer, and then adding a free radical precursor alkyl silicon into the reaction tube; s2, adding dimethyl sulfoxide into the reaction tube, evacuating the reaction tube, exchanging nitrogen, irradiating under a 9W blue light LED lamp, stirring, diluting a reaction solution with ethyl acetate and water, and extracting with ethyl acetate; s3, combining organic phases obtained by extraction, drying by using anhydrous sodium sulfate, filtering again to obtain an organic phase solution, and removing a solvent by using a rotary evaporator; carrying out column chromatography separation by using a mixed solution of petroleum ether and ethyl acetate as an eluting agent; and finally, distilling by using a rotary evaporator to obtain the product N-alkylphthalimide. The N-alkyl phthalimide can be efficiently prepared through the method, the production efficiency is high, and byproducts are few.

Description

technical field [0001] The invention relates to the field of photocatalytic synthesis, in particular to a method for photocatalytic synthesis of N-alkylphthalimide. Background technique [0002] Primary amines are a class of basic and important organic compounds and important intermediates in chemical reactions. The hydrolysis reaction of N-alkylphthalimide is one of the important methods for the synthesis of primary amines, which is called the Gabriel amine synthesis method. Since the synthesis method does not have the problem of side reactions of secondary and tertiary amines, it can be used to synthesize primary amines with higher purity. In the preparation method of N-substituted phthalimide, the commonly used classical method is to react phthalimide with halogenated hydrocarbon under the action of a base (such as reaction formula (1)). However, this synthesis method is suitable for primary halogenated hydrocarbons with high reactivity, while for secondary halogenated ...

Claims

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Application Information

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IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 奚建英方烨汶张莉金小平陈斌张宗勇
Owner NINGBO UNIVERSITY OF TECHNOLOGY
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