Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

A kind of preparation method of 3,4-dimethoxy-n,n-dimethylbenzamide

A technology of dimethylbenzamide and dimethoxybenzene is applied in the field of preparation of chemical intermediate 3,4-dimethoxy-N,N-dimethylbenzamide, and can solve potential safety hazards, The reaction solvent is flammable and explosive, and the reaction yield is only low, so as to achieve the effects of low cost, easy industrialization and simple operation.

Active Publication Date: 2016-04-20
INSIGHT HIGH TECH JIANGSU CO LTD
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method is simple to operate and the reaction conditions are mild, but the reaction yield is only 70%. At the same time, the reaction solvent is extremely flammable and explosive, which has great potential safety hazards and is difficult to scale up 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
  • A kind of preparation method of 3,4-dimethoxy-n,n-dimethylbenzamide
  • A kind of preparation method of 3,4-dimethoxy-n,n-dimethylbenzamide
  • A kind of preparation method of 3,4-dimethoxy-n,n-dimethylbenzamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In the reaction flask, add 138.2g (1.0mol) of 1,2-dimethoxybenzene, 900g of chlorobenzene, cool down to 5°C, add 200.0g of anhydrous aluminum chloride under stirring, add dropwise N,N-dimethoxybenzene Carbamoyl chloride 160.0 g. Insulate and react at 30-50°C for 20 hours. After the reaction is completed, treat with hydrochloric acid. The obtained organic phase is washed twice with 500ml of water. The organic phase is evaporated to dryness. The obtained material is dissolved with 400g of dimethyl carbonate, and then cooled to 0°C and stirred. After 3 hours of crystallization, the solid was obtained by suction filtration, and the weight was 168.4g after drying. The HPLC content: 98.6%, and the yield was 80.5%. 1 HNMR (CDCl 3 , 400MHz) Characterization: δ2.90 (s, 6H, N-CH 3 ), δ3.71 (s, 3H, -OCH 3 ), δ3.75 (s, 3H, -OCH 3 ), δ6.86 (d, 1H, benzene ring-H), δ7.35 (s, 1H, benzene ring-H), δ7.43 (d, 1H, benzene ring-H).

Embodiment 2

[0027] In the reaction flask, add 138.2g (1.0mol) of 1,2-dimethoxybenzene and 700g of chlorobenzene, cool down to 5°C, add 170.0g of anhydrous aluminum chloride under stirring, add dropwise N,N-dimethoxybenzene Carbamoyl chloride 140.0 g. Insulate and react at 30-50°C for 15h, after the reaction is completed, treat with hydrochloric acid, wash the obtained organic phase twice with 500ml of water, evaporate the organic phase to dryness, dissolve the obtained material with 450g of dimethyl carbonate, and then cool down to 0°C and stir After 3 hours of crystallization, the solid was obtained by suction filtration, and the weight was 163.6g after drying. The HPLC content: 98.5%, and the yield was 78.2%. 1 HNMR (CDCl 3 , 400MHz) Characterization: δ2.90 (s, 6H, N-CH 3 ), δ3.71 (s, 3H, -OCH 3 ), δ3.75 (s, 3H, -OCH 3 ), δ6.86 (d, 1H, benzene ring-H), δ7.35 (s, 1H, benzene ring-H), δ7.43 (d, 1H, benzene ring-H).

Embodiment 3

[0029] In the reaction flask, add 138.2g (1.0mol) of 1,2-dimethoxybenzene, 550g of chlorobenzene, cool down to 5°C, add 160.0g of anhydrous aluminum chloride under stirring, add dropwise N,N-dimethoxybenzene Carbamoyl chloride 130.0 g. Insulate and react at 30-50°C for 15 hours, after the reaction is completed, treat with hydrochloric acid, wash the obtained organic phase twice with 500ml of water, evaporate the organic phase to dryness, dissolve the obtained material with 500g of dimethyl carbonate, and then cool down to 0°C and stir After 3 hours of crystallization, the solid was obtained by suction filtration, and the weight was 159.0 g after drying. The HPLC content: 98.5%, and the yield was 76.0%. 1 HNMR (CDCl 3 , 400MHz) Characterization: δ2.90 (s, 6H, N-CH 3 ), δ3.71 (s, 3H, -OCH 3 ), δ3.75 (s, 3H, -OCH 3 ), δ6.86 (d, 1H, benzene ring-H), δ7.35 (s, 1H, benzene ring-H), δ7.43 (d, 1H, benzene ring-H).

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 provides a new preparation method of 3,4-dimethoxy-N,N-dimethylbenzamide. 1,2-dimethoxybenzene, which is relative low in cost, is employed as a raw material in the method and is subjected to a reaction, catalyzed by anhydrous aluminium chloride, with N,N-dimethylaminoformyl chloride. An aimed product (II) is prepared through post-process. The preparation method is low in production cost, is simple and safe in operation and has an industrial production value.

Description

technical field [0001] The invention relates to a preparation method of a chemical intermediate 3,4-dimethoxy-N,N-dimethylbenzamide. Background technique [0002] 3,4-Dimethoxy-N,N-dimethylbenzamide is an important chemical intermediate, and its amide group has special biological activity. Balasubramanian Narasimhan et al reported in European Journal of Medicinal Chemistry, 44(2), 689-700; 2009 that antimicrobial agents can be prepared using it as an intermediate. [0003] About the synthesis of 3,4-dimethoxy-N,N-dimethylbenzamide, literature (1) Chemistry--AEuropeanJournal, 18(32), 9793-9797, S9793 / 1-S9793 / 32; 2012 And literature (2) European Journal of Medicinal Chemistry, 44 (2), 689-700; 2009 are reported. [0004] The synthetic method in document (1) uses 3,4-dimethoxy-benzyl alcohol as a raw material (formula III), and prepares the target product (formula II) by reacting with N, N-dimethylformamide. The reaction equation as follows: [0005] [0006] In this syn...

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): C07C235/46C07C231/12
Inventor 胡圣祥石湘湘袁忠华李冬梅陆黎明罗必奎
Owner INSIGHT HIGH TECH JIANGSU CO LTD
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
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