Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of N-propyl-2-alkynyl phthalimide

A technology of alkynyl phthalimide and alkynyl benzamide, which is applied in the field of preparation of N-propyl-2-alkynyl phthalimide, can solve the problem of low market supply, low supply Low yield, unsuitable for large-scale production, etc.

Pending Publication Date: 2022-05-13
BAYECAO HEALTH IND RES INST (XIAMEN) CO LTD
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But above-mentioned synthetic method all has the problem of low yield, is not suitable for large-scale production, and this is one of important factors that causes the marketization supply of N-propyl-2-alkynyl phthalimide to be few

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of N-propyl-2-alkynyl phthalimide
  • Preparation method of N-propyl-2-alkynyl phthalimide

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0023] The invention provides a kind of preparation method of N-propyl-2-alkynyl phthalimide, comprising the following steps:

[0024] (1) 2-formic acid phenylacetic acid is mixed with acetic anhydride, and dehydration reaction is carried out to obtain phthalic anhydride;

[0025] (2) The phthalic anhydride, propargylamine and phthalic anhydride good solvent are mixed, and ammonolysis reaction is carried out to obtain N-propyl-2-alkynyl benzamide-2-acetic acid;

[0026] (3) The N-propyl-2-alkynyl benzamide-2-acetic acid is mixed with a good solvent of N-propyl-2-alkynyl benzamide-2-acetic acid, and a ring-forming reaction is carried out to obtain N -Propyl-2-ynylphthalimide.

[0027] In the present invention, unless otherwise specified, the raw materials used are commercially available products well known to those skilled in the art.

[0028] The present invention mixes 2-formic acid phenylacetic acid and acetic anhydride for dehydration reaction to obtain phthalic anhydride...

Embodiment 1

[0037] (1) Add 1mol 2-formic acid phenylacetic acid and 25mol acetic anhydride to the reactor and stir evenly, then raise the temperature of the reactor to 80°C for reflux reaction for 3 hours, and monitor the reaction progress by TLC; after the reaction, cool the reactor to room temperature , and then the reaction solution was rotary evaporated at 35° C. to remove acetic anhydride to obtain a crude product, and then washed the crude product solid with 10 mL of petroleum ether to remove residual acetic anhydride on the surface to obtain phthalic anhydride. The yield was 88.90%, and the purity was 99%.

[0038] (2) Add 5g of phthalic anhydride and 25mL of tetrahydrofuran into the reactor and stir evenly, then add 2g of propargylamine dropwise to the solution at a rate of 10mL / min, after the addition is complete, react at 30°C for 12h, TLC The progress of the reaction was monitored; after the reaction was completed, the reaction solution was rotary evaporated at 35° C. to remove...

Embodiment 2

[0041] (1) Add 1mol 2-formic acid phenylacetic acid and 20mol acetic anhydride to the reactor and stir evenly, then raise the temperature of the reactor to 75°C for reflux reaction for 4 hours, and monitor the reaction progress by TLC; after the reaction, cool the reactor to room temperature , and then the reaction solution was rotary evaporated at 38° C. to remove acetic anhydride to obtain a crude product, and then the crude product solid was washed with 8 mL of petroleum ether to remove residual acetic anhydride on the surface to obtain phthalic anhydride. The yield was 87.60%, and the purity was 98.7%.

[0042] (2) Add 4g of phthalic anhydride and 20mL of methanol into the reactor and stir evenly, then add 1.7g of propargylamine dropwise to the solution at a rate of 12mL / min, after the addition is complete, react at 35°C for 13h, The progress of the reaction was monitored by TLC; after the reaction was completed, the reaction solution was rotary evaporated at 38° C. to rem...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
purityaaaaaaaaaa
Login to View More

Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of N-propyl-2-alkynyl phthalimide. The preparation method of the N-propyl-2-alkynyl phthalimide provided by the invention comprises the following steps: mixing 2-formic acid phenylacetic acid with acetic anhydride, and carrying out a dehydration reaction to obtain phthalic anhydride; mixing the phthalic anhydride, propargylamine and a phthalic anhydride good solvent, and carrying out ammonolysis reaction, so as to obtain N-propyl-2-alkynyl benzamide-2-acetic acid; and mixing the N-propyl-2-alkynyl benzamide-2-acetic acid with a good solvent of the N-propyl-2-alkynyl benzamide-2-acetic acid, and carrying out a ring formation reaction, so as to obtain the N-propyl-2-alkynyl phthalimide. The preparation method of the N-propyl-2-alkynyl phthalimide, provided by the invention, has the advantages of high product yield, high purity, simple steps and low production cost, and has a prospect of large-scale industrial application.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of N-propyl-2-ynyl phthalimide. Background technique [0002] N-propyl-2-ynyl homophthalimide (C 12 h 9 NO 2 ) is a propargyl ketone compound, because of its special structure of acetylenic bond and carbonyl bifunctional group, propargyl ketone compound as a highly reactive substrate can perform Michael addition with various nucleophiles to generate other Molecules with complex structures. Therefore, propargyl ketones have always been considered as key intermediates in the synthesis of natural products and complex compounds, and play an important role in many fields such as biomedicine, organic functional materials, pesticides and fuels. [0003] At present, the synthesis of propargyl ketones mainly includes the following methods: (1) coupling of acetylenide and acid halide to synthesize propargyl ketone compound; (2) carbonylation c...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/24
CPCC07D217/24
Inventor 汤须崇赵应伟谢嘉斌宋航余忠钟
Owner BAYECAO HEALTH IND RES INST (XIAMEN) CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products