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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
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  • 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

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  • 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

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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).

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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

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Application Information

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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
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