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

Preparation method of 3-n-butylamine-4-bromo-N-phenylmaleimide

A maleimide and n-butylamine-based technology, applied in the field of preparation of maleimide compounds, can solve the problems of harsh reaction conditions, high reaction temperature, long reaction time and the like, and achieves short reaction route, The effect of simple reaction operation and low cost

Inactive Publication Date: 2016-12-21
DONGHUA UNIV
View PDF0 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In above-mentioned two kinds of synthetic methods, method one needs multiple processes such as bromination, oxidative debromination, amination, steps are many, and reaction time is long; Method two reaction time is long, and reaction temperature is high, and the participation of acetic acid makes raw material easy polymerization, more by-products
[0003] In summary, the above method has the disadvantages of long reaction route, low yield and harsh reaction conditions, and the cost is relatively high in large-scale production.

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 3-n-butylamine-4-bromo-N-phenylmaleimide
  • Preparation method of 3-n-butylamine-4-bromo-N-phenylmaleimide
  • Preparation method of 3-n-butylamine-4-bromo-N-phenylmaleimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Take 17.3g (0.1mol) of N-phenylmaleimide, 8.0g (0.11mol) of n-butylamine and 22.3g (0.1mol) of copper bromide into a 500mL round-bottomed flask, add 1,4-bis 200mL of oxane, heated at 100℃ and stirred for 2h. After the reaction is complete, add 100mL of water, stir for 10 minutes, extract with ethyl acetate (200mL×3), dry the organic phase with anhydrous sodium sulfate, concentrate and evaporate the organic solvent to obtain a yellow-brown solid. Recrystallized from 95% (v / v) ethanol to obtain 27.1 g of a yellow solid, with a yield of 84%, mp: 78-80°C. The proton nuclear magnetic resonance spectrum and carbon spectrum of 3-n-butylamino-4-bromo-N-phenylmaleimide are shown as figure 1 with figure 2 Shown.

Embodiment 2

[0032] Take 1.73g (0.01mol) of N-phenylmaleimide, 0.8g (0.011mol) of n-butylamine and 3.35g (0.015mol) of copper bromide into a 250mL round-bottom flask, add 1,4-bis 80mL of oxane, heated at 100℃ and stirred for 2h. After the reaction is complete, add 100mL of water, stir for 10 minutes, extract with ethyl acetate (100mL×3), dry the organic phase with anhydrous sodium sulfate, concentrate and evaporate the organic solvent to obtain a yellow-brown solid. Recrystallized from 95% (v / v) ethanol to obtain 2.97 g of yellow solid, yield 92%, mp: 78-80°C.

Embodiment 3

[0034] Take 1.73g (0.01mol) of N-phenylmaleimide, 0.8g (0.011mol) of n-butylamine and 3.35g (0.015mol) of copper bromide into a 250mL round-bottom flask, add 1,4-bis 80mL of oxane, heated at 60℃ and stirred for 2h. After the reaction is complete, add 100mL of water, stir for 10 minutes, extract with ethyl acetate (100mL×3), dry the organic phase with anhydrous sodium sulfate, concentrate and evaporate the organic solvent to obtain a yellow-brown solid. Recrystallized from 95% (v / v) ethanol to obtain 2.74 g of a yellow solid, with a yield of 85%, mp: 78-80°C.

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 relates to a preparation method of 3-n-butylamine-4-bromo-N-phenylmaleimide. the preparation method comprises the following steps: adding N-phenylmaleimide, n-butylamine and a brominating agent into a solvent, reacting at room temperature of minus 100 DEG C for 1-3 h, adding water and stirring after the end of the reaction, extracting, drying, concentrating, and recrystallizing to obtain 3-n-butylamine-4-bromo-N-phenylmaleimide. Yield of 3-n-butylamine-4-bromo-N-phenylmaleimide is high; reaction operation is simple; reaction route is short; and there is less ''three wastes'' (waste gas, wastewater and residue). The preparation method is easy for industrial production.

Description

Technical field [0001] The invention belongs to the field of preparation of maleimide compounds, and particularly relates to a preparation method of 3-n-butylamino-4-bromo-N-phenylmaleimide. Background technique [0002] 3-Amino-4-bromomaleimide and its derivatives are important intermediates for drug synthesis. The intermediates can be used to synthesize 3-amino-4-arylmaleimide compounds. , Antiviral and inhibition of protein kinases have important applications (Budke, B.; Kalin, JH; Pawlowski, M.; Zelivianskaia, AS; Wu, M.; Kozikowski, AP; Connell, PPJ Med. Chem., 2013 , 56:254-263. and Awuah, E.; Capretta, AJOrg. Chem., 2011, 76:3122-3130.). In addition, in recent years, the application of fluorescent materials and fluorescent probes has also been studied (Mabire, AB; Robin, MP; Quan, WD; Willcock, H.; Stavros, VG; O'Reilly, RKChem. Commun. ,2015,51:9733-9736.). It is reported in the literature that the synthetic methods of 3-amino-4-bromomaleimide compounds mainly include ...

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): C07D207/456
CPCC07D207/456
Inventor 赵圣印安玉龙
Owner DONGHUA UNIV
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