Synthesis of asymmetric dipyridyl substituted urea derivatives

A symmetrical dipyridyl and synthetic method technology, which is applied in the field of synthesizing unsymmetrical dipyridyl substituted urea derivatives, selenium or selenium dioxide catalytic carbonylation, can solve the problem of phosgene being highly toxic, corrosive to equipment, and easy to pollute the environment and other problems, to achieve the effect of easy clean production, mild reaction conditions, and less investment in equipment

Inactive Publication Date: 2004-07-07
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
View PDF14 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the conventional method for synthesizing pyridine urea derivatives mainly adopts phosgene or phosgene-like isocyanate method. The disadvantage is that phosgene is highly toxic, and a large amount of corrosive chlorine-containing by-products are produced in the reaction process, which not only severely corrodes The equipment is also easy to pollute the environment
Moreover, the conventional

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
  • Synthesis of asymmetric dipyridyl substituted urea derivatives
  • Synthesis of asymmetric dipyridyl substituted urea derivatives
  • Synthesis of asymmetric dipyridyl substituted urea derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Synthesis of 1-(2-pyridyl)-3-(6-methoxy-3-pyridyl)urea under selenium catalysis

[0029] Add 2-methoxy-5-nitropyridine (10mmol), selenium (0.5mmol), 2-aminopyridine (10mmol), triethylamine (10mmol) and toluene 10ml into a 100ml stainless steel autoclave, replace with CO After three times, raise the CO pressure to 3.0MPa, put it in an oil bath at 130°C and stir for 4 hours, cool to room temperature, filter the reaction product, and purify the filtered crystals by column chromatography, the eluent is petroleum ether : Ethyl acetate (1:1), the eluate was concentrated to obtain the product, m.p.178~180°C, the yield was 74.5%.

Embodiment 2

[0030] Example 2 Synthesis of unsymmetrical dipyridyl substituted urea derivatives under selenium catalysis

[0031] Embodiment is summarized as follows in tabular form: (its reaction condition and step are with embodiment 1)

[0032]

[0033] Table 1: Selenium-catalyzed carbonylation of 2-methoxy-5-nitropyridine with aminopyridine derivatives

[0034] Reactive Synthesis of Unsymmetrical Bipyridine Urea Derivatives

[0035] sequence

[0036] Melting point Yield

[0037] Substrate Product

[0038] No

[0039] (°C) (%)

[0040]

Embodiment 3

[0041] Example 3 Synthesis of 1-(2-pyridyl)-3-(6-methoxy-3-pyridyl)urea catalyzed by selenium dioxide

[0042] Add 2-methoxy-5-nitropyridine (10mmol), selenium dioxide (0.5mmol), 2-aminopyridine (10mmol), triethylamine (10mmol) and toluene 10ml in the stainless steel autoclave of 100ml, use After CO replacement for three times, raise the pressure of CO to 3.0 MPa, put it in an oil bath at 130°C and stir for 4 hours, cool to room temperature, filter the reaction product, and purify the filtered crystals by column chromatography. The eluent is Petroleum ether: ethyl acetate (1:1), the eluate was concentrated to obtain the product, m.p.178-180°C, the yield was 77.1%.

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

No PUM Login to view more

Abstract

A process for synthesizing the unsymmetrical dipyridinyl substituted urea derivative features the reaction between aminopyridine derivative, nitropyridine derivative, Se or SeO2 as catalyst, and triethylamine as cocatalyst in organic solvent at 50-200 deg.C in a sealed high-pressure reactor for 2-20 hr. Its advantages are simple process and high output rate.

Description

technical field [0001] The invention relates to a synthesis method of unsymmetrical dipyridyl substituted urea derivatives, in particular to a selenium or selenium dioxide catalyzed carbonylation method for synthesizing unsymmetrical dipyridyl substituted urea derivatives. technical background [0002] Pyridine urea derivatives containing peptide bonds (-CONH-) have certain biological and physiological activities. For example, N-benzoyl-N'-pyridyl urea derivatives are a class of high-efficiency insecticides [Documents: US4,405,552; EP8,880; DE3,126,263; US4,264,605; JP62,155,260; JP55,011,537; CA1,131,232, etc.]; N-phenyl-N'-pyridyl urea derivatives are an important class of herbicides and plant growth regulators [Document: EP401,168; US438,054; Plant Physiology Communication, 1989, ( 1), 17~19, etc.]; N-phenyl-N'-nitrogenated pyridyl urea derivatives are also a class of efficient plant growth regulators [Documents: US4,787,931; WO8,702,665; WO8,403,884 Wait】. In conventi...

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
IPC IPC(8): C07D401/12
Inventor 陈金铸凌冈陆世维
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap