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

Synthetic method of 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine

A technology of methoxyphenyl and hydroxyphenyl, which is applied in the synthesis field of fine chemicals, can solve problems such as difficulty in dispersing and shortening reaction time, and achieve improved purity and yield, high utilization rate of raw materials, and wide application foreground effect

Inactive Publication Date: 2016-03-30
EAST CHINA NORMAL UNIV
View PDF8 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These two kinds of methods all do not need to add solvent in addition, and the reaction time obviously shortens, but the first step reaction is because gained product is the mixture of intermediate and benzoic acid, and both fusing points are all higher than 170 ℃, both solidify rapidly during cooling and make The product is clumped together, it is difficult to break up, and the power of the agitator is required to reach a certain speed, but this is difficult in industrial 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
  • Synthetic method of 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine
  • Synthetic method of 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Preparation of intermediate 2-(4-methoxyphenyl)-4 hydrogen-1,3-benzoxazin-4-one

[0034]In a 100mL three-necked flask, add 5g of salicylamide to 13.1g (10.4mL) of 4-methoxybenzoyl chloride at room temperature, and stir at this temperature for 15min (at this time, the reaction solution is a slightly yellow suspension) . Then the temperature is raised to 150-160°C (no strict temperature requirement), and the reaction is kept for one hour (completely dissolved at about 100°C, showing a red clear liquid).

[0035] After the detection reaction is completed, put the material into the flat tray while it is hot. After cooling, it was crushed and used directly in the next reaction to obtain 14.7 g of crude product, which contained 9.2 g of intermediate, and the yield was close to 100%. Elemental Analysis: C 15 h 11 NO 3 : Requires: C71.14%; H4.38%; N5.53%; O18.95%

[0036] Found: C70.94%; H4.43%; N5.42%; O18.99%

Embodiment 2

[0037] Example 2: Preparation of 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine

[0038] Add 750mL of methanol and 20.4g of 30% sodium methoxide into a 1000mL four-necked bottle, stir well, add 5.71g of benzamidine hydrochloride, stir at room temperature for 30min, then add 14.5g at 25°C at one time (slowly add , depending on the exothermic situation) the intermediate in the previous step, after stirring for 30min, the temperature was raised to reflux and kept for 3h. After the TLC detection reaction is completed, cool to 30°C and filter, the filtrate contains methanol / sodium methoxide and can be used directly (apply several times until the impurities increase, the methanol can be evaporated, and the recovery can be applied); the filter cake is washed with water to remove salt, and the salt solution is 30% hydrochloric acid Adjust the pH to 7-8 and stir for 30 minutes (p-methoxybenzoic acid can be recovered); the filter cake is filtered and then washed with me...

Embodiment 3

[0041] Example 3: Preparation of 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine

[0042] Add 375mL of methanol (applicable) and 10.2g of 30% sodium methoxide to a 500mL four-necked bottle, stir well, add 2.86g of benzamidine hydrochloride, stir at room temperature for 30min, then add 7g at 60°C at one time (required for trial production) Slowly add, depending on the exothermic situation) the intermediate in the previous step, stir for 30min, then heat up to reflux and keep for 3h. After the TLC detection reaction is completed, cool to 30°C and filter, the filtrate contains methanol / sodium methoxide and can be used directly (apply several times until the impurities increase, the methanol can be evaporated, and the recovery can be applied); the filter cake is washed with water to remove salt, and the salt solution is 30% hydrochloric acid After adjusting the pH to 7-8, stir for 30 minutes (p-methoxybenzoic acid can be recovered); after the filter cake is filtere...

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

The invention discloses a synthetic method of a compound 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine. The synthetic method comprises the following steps: 4-methoxybenzoyl chloride and salicylamide are added to a reaction kettle, are stirred for 15 min at the room temperature, are heated to 150-160 DEG C and react for 0.5-1 h, a product is discharged to a tray while being hot, crude 2-(4-methoxyphenyl)-tetrahydro-1,3-benzoxazine-4-one is obtained through crushing after cooling and is added to a uniformly stirred methanol / sodium methoxide mixed solution of benzamidine hydrochloride at the room temperature, the mixture is heated to backflow and cooled to 30 DEG C for filtering after reaction, a filter cake is washed with water, drained, subjected to stirring washing once with methanol and dried at 60 DEG C for 3 h, and 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine is obtained. The synthetic method has the advantages of simplicity in operation, mild conditions, short reaction time, low production cost and high yield.

Description

technical field [0001] The present invention relates to a synthesis method of fine chemicals, especially a kind of 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-tri Synthetic method of oxazine. Background technique [0002] Triaryl triazine compounds are well-developed high-efficiency ultraviolet absorbers with good absorption performance and anti-oxidation ability, and are widely used in industries such as plastics, films, coatings and cosmetics. Molecular formula C of 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine 22 h 17 N 3 o 2 , the molecular weight is 355.39, and its structural formula is as follows: [0003] [0004] In the prior art, the synthetic method of 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine, for example, document (1) (Heterocyclicdioxethane substrates, Process for their preparation and their use US6107036) disclosed the first step: adding pyridine to the suspension of salicylamide and xylene, heating to...

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): C07D251/24
CPCC07D251/24
Inventor 王轶路洪镛裕
Owner EAST CHINA NORMAL 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