Method for synthesizing multi-substituted benzene by one reactor method

A multi-substitution and benzo technology, applied in organic chemistry and other fields, can solve the problems of cumbersome transformation steps and achieve the effects of simple operation, good water resistance and air stability, and cheap and easy synthesis

Inactive Publication Date: 2007-08-29
SHAANXI NORMAL UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] From the perspective of traditional methods, the introduction of substituent groups on the benzene ring usually requires multi-step transformations, and the transformation steps required to introduce more and different groups will be more cumbersome

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 multi-substituted benzene by one reactor method
  • Method for synthesizing multi-substituted benzene by one reactor method
  • Method for synthesizing multi-substituted benzene by one reactor method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Compound 1: Add 15 ml of acetonitrile, raw material 1 (0.168 g, 1 mmol) and raw material 2 (0.149 g, 1 mmol) into a dry flask, stir well to completely dissolve the substrate, heat up to 60°C, add Sodium ethoxide (68 mg, 1 mmol, 100%), under vigorous stirring to completely dissolve the sodium ethoxide. The reaction mixture was kept warm (100°C) until the reaction of starting materials was complete (2 hours). After cooling to room temperature, the solvent was distilled off and separated by column chromatography (petroleum ether: ethyl acetate = 6:1) to obtain a pale yellow solid.

[0026] The physical and chemical properties of compound 1 prepared in this example are as follows after testing: yield: 76%, melting point: 204.2-205.8°C;

[0027] Referring to Fig. 1a, the H of the compound 1 of the present embodiment is tested with a nuclear magnetic resonance instrument and the results are as follows: 1 H NMR (300MHz, CDCl 3 )δ (ppm) 5.81 (s, 2H), 6.74-7.51 (m, 11H);

[...

Embodiment 2

[0092] Compound 1: Add 15 ml of ethanol, raw material 1 (0.168 g, 1 mmol) and raw material 2 (0.149 g, 1 mmol) into a dry flask, stir well to completely dissolve the substrate, heat up to 60°C, add Sodium ethoxide (68 mg, 1 mmol, 100%), under vigorous stirring to completely dissolve the sodium ethoxide. The reaction mixture was kept at 60°C until the reaction of starting materials was completed (5 hours). After cooling to room temperature, the solvent was distilled off and separated by column chromatography (petroleum ether: ethyl acetate = 6:1) to obtain a pale yellow solid. Yield: 54%.

[0093] Substitute raw material 1 with raw material 2~14, its charging ratio is identical with compound 1, can obtain respectively compound 2 (productive rate 53%), compound 3 (productive rate 52%), compound 4 (productive rate 56%), compound 5 ( Yield 55%), compound 6 (yield 58%), compound 7 (yield 56%), compound 8 (yield 57%), compound 9 (yield 49%), compound 10 (yield 51%) , compound 11 ...

Embodiment 3

[0095] Compound 1: Add 15 ml of chloroform, raw material 1 (0.168 g, 1 mmol) and raw material 2 (0.149 g, 1 mmol) into a dry flask, stir well to completely dissolve the substrate, heat up to 60°C, add Sodium methoxide (54 mg, 1 mmol, 100%), the sodium methoxide was completely dissolved under vigorous stirring. The reaction mixture was kept warm (80°C) until the reaction of starting materials was complete (24 hours). After cooling to room temperature, the solvent was distilled off and separated by column chromatography (petroleum ether: ethyl acetate = 6:1) to obtain a pale yellow solid. Yield: 37%.

[0096] Substitute raw material 1 with raw material 2~14, its charge ratio is identical with compound 1, can obtain compound 2 (productive rate 33%), compound 3 (productive rate 32%), compound 4 (productive rate 40%), compound 5 ( Yield 35%), compound 6 (yield 38%), compound 7 (yield 36%), compound 8 (yield 37%), compound 9 (yield 40%), compound 10 (yield 41%) , compound 11 (yie...

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
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to view more

Abstract

The invention relates to a polysubstitution benzene and polysubstitution benzene paraheteocycle compound and the method to compound. The invention has the advantages of easy to operate and strong feasibility. The product is the medicine intermediate of a crucial medicine and the analogue. It has crucial application value in medicine filtering and pharmacy industrial.

Description

technical field [0001] The invention relates to a multi-substituted benzene and a multi-substituted benzo heterocyclic compound and an effective method for synthesizing a multi-substituted benzene and a multi-substituted benzo heterocyclic compound. Using the method, a simple one-pot method can be used to synthesize multiple positions Benzene rings with the same or different substituents. Background technique [0002] From the perspective of traditional methods, the introduction of substituent groups on the benzene ring usually requires multi-step transformations, and the transformation steps required to introduce more and different groups will be more cumbersome. For example, the application of positioning groups (such as the sulfonic acid group can control the reaction at the meta-position, the amino group and the alkoxy group can control the reaction at the ortho-position and the para-position, etc.) needs to introduce and remove the positioning group. So more often, the...

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): C07C255/63C07D311/80C07D307/54C07D333/24
Inventor 李捷薛东张尊听
Owner SHAANXI NORMAL UNIV
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