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Preparation method of 2-methyl-1,2,3,9-tetrahydro-benzo[b]pyrrole[1,4]-thiazine-1,3-diketone compound

A technology of tetrahydrobenzene and compounds, which is applied in the field of pharmaceutical intermediates and its preparation, can solve the problems of difficult acquisition of raw materials, long reaction routes, and low yields, and achieve the effects of low cost, short reaction routes, and high yields

Inactive Publication Date: 2016-11-16
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] In summary, the above method has disadvantages such as long reaction route, low yield and difficult access to raw materials, and the cost is relatively high in large-scale production.

Method used

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  • Preparation method of 2-methyl-1,2,3,9-tetrahydro-benzo[b]pyrrole[1,4]-thiazine-1,3-diketone compound
  • Preparation method of 2-methyl-1,2,3,9-tetrahydro-benzo[b]pyrrole[1,4]-thiazine-1,3-diketone compound
  • Preparation method of 2-methyl-1,2,3,9-tetrahydro-benzo[b]pyrrole[1,4]-thiazine-1,3-diketone compound

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Experimental program
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Effect test

Embodiment 1

[0040] Take 1.3g (0.01mol) of o-aminothiophenol, 1.1g (0.01mol) of N-methylmaleimide, and 0.19g (0.001mol) of cuprous iodide, and add them to a 100mL round-bottomed flask. Oxygen, then add N,N-dimethylformamide (DMF) 10mL, keep 120°C for 8 hours, after the reaction is complete, add 30mL of water, stir for 5 minutes, extract with ethyl acetate 50mL×3, dry the organic phase, and use 95% ethanol Crystallization gave 1.22 g of yellow solid 2-methyl-1,2,3,9-tetrahydrobenzo[b]pyrrole[1,4]-thiazine-1,3-dione, yield 52.6%, mp: 236~238℃.

Embodiment 2

[0042]Take 5.0g (0.04mol) of o-aminothiophenol, 8.9g (0.08mol) of N-methylmaleimide, and 7.6g (0.04mol) of cuprous iodide, and add them to a 100mL round-bottomed flask. Oxygen, then add 60mL of N,N-dimethylacetamide (DMA), keep at 120°C for 12h, after the reaction is complete, add 100mL of water, stir for 5 minutes, extract with 100mL×3 ethyl acetate, dry the organic phase, and use 95% ethanol Crystallization gave 7.8 g of yellow solid 2-methyl-1,2,3,9-tetrahydrobenzo[b]pyrrole[1,4]-thiazine-1,3-dione, yield 85.3%, mp: 237~240℃.

Embodiment 3

[0044] Take 5.0g (0.04mol) of o-aminothiophenol, 4.4g (0.04mol) of N-methylmaleimide, and 3.8g (0.02mol) of cuprous iodide, and add them to a 100mL round-bottomed flask. Oxygen, then add 50mL of N,N-dimethylformamide (DMF), keep at 120°C for 10h, after the reaction is complete, add 50mL of water, stir for 5 minutes, extract with 100mL×3 ethyl acetate, dry the organic phase, and use 95% ethanol Crystallization gave 7.4 g of yellow solid 2-methyl-1,2,3,9-tetrahydrobenzo[b]pyrrole[1,4]-thiazine-1,3-dione, yield 80.5%, mp: 237~239℃.

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Abstract

The invention relates to a preparation method of a 2-methyl-1,2,3,9-tetrahydro-benzo[b]pyrrole[1,4]-thiazine-1,3-diketone compound which has a following structural formula (please see the formula in the description). The preparation method comprises the steps that o-aminobenzenethiol, N-methylmaleimide and a catalyst are added into a solvent, oxygen is introduced, the materials are heated to 25 DEG C to 160 DEG C to react for 4 hours to 24 hours, purification is conducted, and then the 2-methyl-1,2,3,9-tetrahydro-benzo[b] pyrrole[1,4]-thiazine-1,3-diketone compound is obtained. According to the 2-methyl-1,2,3,9-tetrahydro-benzo[b]pyrrole[1,4]-thiazine-1,3-diketone prepared through the method, the yield is high, reaction operation is easy, the reaction route is short, an oxidizing agent is green and natural, few three wastes are generated, and industrialized production is easy to achieve.

Description

technical field [0001] The invention belongs to the field of pharmaceutical intermediates and their preparation, in particular to a 2-methyl-1,2,3,9-tetrahydrobenzo[b]pyrrole[1,4]-thiazine-1,3-bis Preparation methods of ketone compounds. Background technique [0002] 2-Methyl-1,2,3,9-tetrahydrobenzo[b]pyrrole[1,4]-thiazine-1,3-dione (I) and its derivatives are important pharmaceutical intermediates At the same time, it has a very wide range of antibacterial activities, especially for Gram-negative bacteria (Igarashi, Y.; Watanabe, S. Preparation of 1,4-benzothiazine-2,3-dicarboximides via intramolecular cyclization of N -substituted 2-[(2-acylaminophenyl)thio]maleimides and investigation of their antibacterial activity. Nippon. Kagaku Kaishi. 1992, 11, 1392-1396.). [0003] It is reported in the literature that the synthesis methods of 1,2,3,9-tetrahydrobenzo[b]pyrrole[1,4]-thiazine-1,3-dione compounds mainly include three kinds: [0004] Method 1 Using o-aminothiophenol ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04
CPCC07D513/04
Inventor 赵圣印杨振华
Owner DONGHUA UNIV
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