CN106518705A

CN106518705A - Synthesis of acetoacetanilide

Info

Publication number: CN106518705A
Application number: CN201610967247.XA
Authority: CN
Inventors: 王绚
Original assignee: Shandong Gao Jie Environmental Protection Technology Co Ltd
Current assignee: Shandong Gao Jie Environmental Protection Technology Co Ltd
Priority date: 2016-10-28
Filing date: 2016-10-28
Publication date: 2017-03-22

Abstract

The invention relates to synthesis of acetoacetanilide. The synthesis comprises the following steps: weighing 5.31 mmol of ethyl acetoacetate, 5.31 mmol of phenylamine and 0.531 mmol of 4-dimethylamino pyridine, adding the weighed materials into a single-opening bottle with the volume of 25 mL, then adding 10 to 30 mL of methylbenzene, performing heating reflux under stirring for 20 to 36 hours, monitoring the raw materials by using thin layer chromatography (petroleum ether: ethyl acetate=4: 1, and Rf=0.37), ending the reaction after the raw materials disappear, adding water, transferring a reaction solution into a separating funnel, performing extracting with ethyl acetate (20 mL x 3), performing collecting to obtain an organic phase, washing the organic phase with saturated sodium chloride, performing drying with anhydrous MgSO4, performing filtering to remove solids, collecting the obtained filtrate, performing rotary evaporateion on the filtrate, and performing column chromatography separation with a mixture (petroleum ether: ethyl acetate=10: 1) serving as an eluent to obtain acetoacetanilide which is a target compound.

Description

The synthesis of alpha.-acetylacetanilide

Technical field

The present invention relates to the synthesis of alpha.-acetylacetanilide, belongs to synthesis chemical field.

Background technology

As multi-component reaction has, simple to operate, Atom economy is high, resource utilization is high, explore energy height, convergence Property it is high the features such as, it can reduce chemical contamination to greatest extent, be more nearly the concept of preferable synthesis, be greenization at this stage Learn an important focus of research so as to there is very important status in modern organic synthesis chemistry, be that current chemistry is sent out One of field the most active in exhibition.

Chromene compound has extensive physiologically active and pharmacologically active, is heterocycle of the class in nature generally existing Framework compound.Research finds, 2- virtue imido grpup chromene analog derivatives by suppressing the activity of relevant enzyme, be expected to become treatment Ah A kind of approach of the diseases such as Zi Haimo diseases, cancer, attracts attention and research；Additionally, 2- virtue imido grpup chromenes derive Thing has also shown great application prospect, its hypotoxicity and specific marker on active somatic cell labelling as fluorescent material The advantage of organelle so as to shown great application prospect in terms of bioanalysiss research.Therefore, easy, efficient, fast It is the important directions for studying such compound to synthesize such compound under conditions of speed, economy.

The content of the invention

The technical problem to be solved is to provide the synthesis of alpha.-acetylacetanilide, and technical scheme is as follows：Weigh second Ethyl acetoacetic acid ethyl ester 5.31mmol, aniline 5.31mmol, and DMAP 0.531mmol are added in 25mL single port bottles, Then 10-30mL toluene is added, heated and stirred backflow 20-36h utilizes thin layer chromatography (petroleum ether: ethyl acetate=4: 1Rf= 0.37), after monitoring raw material disappearance, terminate reaction, add water, reaction solution is transferred in separatory funnel, ethyl acetate (20mL × 3) extract, collect the organic faciess for obtaining, then organic faciess are washed through saturated sodium-chloride, and use anhydrous MgSO₄It is dried, crosses and filter Solid is removed, the filtrate after filtering is collected, and filtrate is rotated, Jing column chromatography petroleum ether: ethyl acetate=10: 1 makees eluant, point From target compound alpha.-acetylacetanilide.

The invention has the beneficial effects as follows：Preparation technology simple environment protection, low cost are applied widely.

Specific embodiment

Embodiment 1

Weigh ethyl acetoacetate 5.31mmol, aniline 5.31mmol, and DMAP 0.531mmol to be added to In 25mL single port bottles, 10mL toluene is then added, heated and stirred backflow 20h, using thin layer chromatography (petroleum ether: ethyl acetate Monitor raw material disappearance after, terminate reaction, add water, reaction solution be transferred in separatory funnel=4: 1Rf=0.37), acetic acid second Ester (20mL × 3) is extracted, and collects the organic faciess for obtaining, and then organic faciess are washed through saturated sodium-chloride, and use anhydrous MgSO₄It is dry Dry, solids removed by filtration is collected the filtrate after filtering, and filtrate is rotated, Jing column chromatography petroleum ether: ethyl acetate=10: 1 makees Eluant, separates to obtain target compound alpha.-acetylacetanilide.

Embodiment 2

Weigh ethyl acetoacetate 5.31mmol, aniline 5.31mmol, and DMAP 0.531mmol to be added to In 25mL single port bottles, 30mL toluene is then added, heated and stirred backflow 36h, using thin layer chromatography (petroleum ether: ethyl acetate Monitor raw material disappearance after, terminate reaction, add water, reaction solution be transferred in separatory funnel=4: 1Rf=0.37), acetic acid second Ester (20mL × 3) is extracted, and collects the organic faciess for obtaining, and then organic faciess are washed through saturated sodium-chloride, and use anhydrous MgSO₄It is dry Dry, solids removed by filtration is collected the filtrate after filtering, and filtrate is rotated, Jing column chromatography petroleum ether: ethyl acetate=10: 1 makees Eluant, separates to obtain target compound alpha.-acetylacetanilide.

Embodiment 3

Weigh ethyl acetoacetate 5.31mmol, aniline 5.31mmol, and DMAP 0.531mmol to be added to In 25mL single port bottles, 20mL toluene is then added, heated and stirred backflow 30h, using thin layer chromatography (petroleum ether: ethyl acetate Monitor raw material disappearance after, terminate reaction, add water, reaction solution be transferred in separatory funnel=4: 1Rf=0.37), acetic acid second Ester (20mL × 3) is extracted, and collects the organic faciess for obtaining, and then organic faciess are washed through saturated sodium-chloride, and use anhydrous MgSO₄It is dry Dry, solids removed by filtration is collected the filtrate after filtering, and filtrate is rotated, Jing column chromatography petroleum ether: ethyl acetate=10: 1 makees Eluant, separates to obtain target compound alpha.-acetylacetanilide.

The foregoing is only presently preferred embodiments of the present invention, not to limit the present invention, all spirit in the present invention and Within principle, any modification, equivalent substitution and improvements made etc. should be included within the scope of the present invention.

Claims

1. the synthesis of alpha.-acetylacetanilide, it is characterised in that include：Weigh ethyl acetoacetate 5.31mmol, aniline 5.31mmol, and DMAP 0.531mmol is added in 25mL single port bottles, then adds 10-30mL toluene, plus Thermal agitation flows back 20-36h, after being disappeared using thin layer chromatography monitoring raw material, terminates reaction, adds water, reaction solution is transferred to point In liquid funnel, the organic faciess for obtaining are collected in ethyl acetate 20mL × 3 extraction, and then organic faciess are washed through saturated sodium-chloride, and Use anhydrous MgSO₄It is dried, solids removed by filtration, collects the filtrate after filtering, and filtrate is rotated, Jing column chromatography petroleum ether: second Acetoacetic ester=10: 1 makees eluant, separate to obtain target compound alpha.-acetylacetanilide.

2. synthetic method according to claim 1, it is characterised in that the thin layer chromatography is petroleum ether: ethyl acetate=4 : 1Rf=0.37.