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

Method for synthesizing 3-(2-phenylethyl)-5-[2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolin-en]-2,4-oxazolidinedione

A technology of phenethyloxazolidine and phenylethyl, applied in 3-(2-phenylethyl)-5-[2,3,6,7-tetrahydro-1H,5H-benzo[ ij] The synthesis field of quinoline-9-ene]-2,4-oxazolidinedione can solve the problems of low total reaction yield, high price of acetoxyacetyl chloride and high production cost, and achieve simple preparation process and low raw material Inexpensive, low-cost effect

Inactive Publication Date: 2011-06-22
NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The method raw material acetoxyacetyl chloride is expensive, the total reaction yield is low (30%), and the production cost is high

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
  • Method for synthesizing 3-(2-phenylethyl)-5-[2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolin-en]-2,4-oxazolidinedione
  • Method for synthesizing 3-(2-phenylethyl)-5-[2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolin-en]-2,4-oxazolidinedione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 1) Add 11.5 grams (0.50 mol) of sodium metal to 250 ml of dry ethanol, add 52 grams (0.50 mol) of ethyl glycolate and 30 grams (0.50 mol) of urea after the reaction of sodium metal is complete, and reflux under stirring After 18 hours, evaporate the ethanol to dryness, add 200 ml of water to the obtained waxy solid, add dropwise 6 mol / L of hydrochloric acid to PH=2, extract 3 times with 200 ml of ethyl acetate each time, combine ethyl acetate, anhydrous sulfuric acid After sodium drying, ethyl acetate was distilled off to obtain 31.3 g of oxazolidine-2,4-dione with a yield of 62% and a melting range of 86.2-88.4°C [literature value: 85.0-88.0°C].

[0018] 2) 20 g (0.20 mol) of oxazolidine-2,4-dione, 44.4 g (0.24 mol) of β-bromophenylethane, and 41.4 g (0.30 mol) of potassium carbonate were added to 200 ml of N, N-dimethyl In methyl formamide, stirring and reacting at 80°C for 15 hours, the excess potassium carbonate was filtered off, the filtrate was added dropwise to w...

Embodiment 2

[0021] 1) with embodiment 1 step 1);

[0022] 2) 20 g (0.20 mol) of oxazolidine-2,4-dione, 44.4 g (0.24 mol) of β-bromophenylethane, and 20.7 g (0.30 mol) of diethylamine were added to 200 ml of N, N-di In methyl acetamide, stirred and reacted at 60°C for 15 hours, filtered off excess potassium carbonate, and added the filtrate dropwise to water, the obtained white precipitate crystallized in ethanol to obtain 3-phenylethyloxazolidine-2,4-di Ketone 28.75 g (0.14 mol), yield 70.0%, melting range 113.8-114.5°C [literature melting point value: 114.0°C].

[0023] 3) Same as embodiment 1 step 3).

Embodiment 3

[0025] 1) with embodiment 1 step 1);

[0026] 2) Add 20 grams (0.20 mol) of oxazolidine-2,4-dione, 44.4 grams (0.24 mol) of β-bromophenylethane, and 31.8 grams (0.30 mol) of sodium carbonate into 200 ml of dimethyl sulfoxide , 120 DEG C of stirring and reacting for 15 hours and filtering off excess sodium carbonate, the filtrate was added dropwise to water, and the white precipitate was crystallized in ethanol to obtain 26.65 grams of 3-phenethyloxazolidine-2,4-dione (0.13mol ), yield 65.0%, melting range 114.0-114.9°C [literature melting point value: 114.0°C].

[0027] 3) Same as embodiment 1 step 3).

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
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a synthesis method of the 3-(2-phenyl ethyl)-5-[2, 3, 6, 7-tetrahydrogen-1H, 5H-dibenzo [ij] quinoline-9-ene]-2, 4-oxazolidine dione; the steps first uses the hydroxy ethyl acetate and urea as the raw materials to make the oxazolidine-2 ,4-dione; then the oxazolidine-2 ,4-dione reacts with the beta-bromophenyl ethane to make the 3-phenethyl-oxazolidine-2, 4-dione; the 3-phenethyl-oxazolidine-2, 4-dione then reacts with the 2,3,6,7-tetrahydrogen-1 H, 5H-pyrido [3,2,1-ij] quinoline-9-formaldehyde to make the product 3-(2-phenyl ethyl)-5-[2,3,6, 7-tetrahydrogen-1 H, 5H-benzo [ij] quinoline-9-ene]-2,4-oxazolidine dione. The invention is of the simple process, the easily accessible and cheap raw materials, the high production rate, the low cost and the suitableness forthe industrial production.

Description

technical field [0001] The present invention relates to 3-(2-phenylethyl)-5-[2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoline-9-ene]-2,4-oxa Synthetic method of oxazolidinedione. Background technique [0002] CTP (computer-to-plate) technology can be divided into thermal and photosensitive two categories. Photosensitive plate-making technology has the advantage of being easy to master and has been widely used in Europe and Japan. In the photosensitive technology, the semiconductor laser source made of indium gallium nitride (InGaN) has a simple structure, long life and low cost. It has entered the practical stage and will gradually replace the original argon ion laser source (Ar laser) and solid-state laser. Source (FD-YAG laser). Since the InGaN semiconductor laser source produces short-wavelength laser light from 350nm to 450nm, the development of photosensitive compounds with sufficient sensitivity in this wavelength range is the key to expanding the application of semicond...

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 Patents(China)
IPC IPC(8): C07D455/04
Inventor 骆成才张华星杨志杰
Owner NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com