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Preparation of 5,6-dihydro-6-methieno [2,3-b] thiopyran-2-sulfonic acid amide-4-keto

A technology of methyl thiophene and sulfonamide, applied in organic chemistry, antibacterial drugs, etc., can solve the problems of incomplete organic preparation methods, etc., and achieve the effects of stable reaction, easy scale-up production, and strong effect

Inactive Publication Date: 2009-08-12
上饶京新药业有限公司 +1
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Problems solved by technology

There are not many studies on this compound abroad, and there is no complete preparation method for synthesizing this organic compound; there is no report on its synthesis in China

Method used

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  • Preparation of 5,6-dihydro-6-methieno [2,3-b] thiopyran-2-sulfonic acid amide-4-keto

Examples

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Embodiment Construction

[0013] 1. Preparation of lithium thiophene-2-thiolate

[0014] In a clean and dry 500 ml four-neck flask, add 10.5 g (0.125 moles) of thiophene and 150 ml of tetrahydrofuran, cool to -20°C, add dropwise 63 ml of 2 moles per liter of butyllithium in pentane for about 10 minutes The dropwise addition is complete. A yellow solution was obtained and stirring was continued for 1 hour at -20°C. Add 4.01 g (0.125 mol) of sulfur to obtain an orange solution, then continue to stir the reaction at -20°C until the HPLC tracking reaction is complete;

[0015] 2. Preparation of intermediate product 5,6-dihydro-6-methylthieno[2,3-b]thiopyran-4-one

[0016] Add 10.8 g (0.125 mol) of (R)-β-butyrolactone into the above four-neck flask with a syringe, the solution turns orange, and the temperature is slowly raised to room temperature. The tetrahydrofuran was evaporated, the remaining orange gum was suspended in 70 ml of toluene, 1 mole of hydrochloric acid per liter was added dropwise under ...

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Abstract

The invention relates to a preparation method of 5,6-dihydro-6-methylthieno(2,3-b) thiopyran-2-sulfamide-4-ketone, which is characterized by comprising the following processing steps of: adding 0.125 mol of thiophene and 150 milliliter of tetrahydrofuran in a four-hole flask, and cooling down to -20 DEG C; dropwise adding 63 milliliter of 2 mol / liter butyl lithium pentane solution, and adding 0.125 mol of sulfur and 0.125 mol of (R)-beta-butyrolactone; when heating to room temperature, adding 0.125 mol of trifluoro acetic anhydride, and carrying out mechanical intense stirring; after the completion of reaction, slowly adding the mixture in a flask containing 0.166 mol of chlorosulfonic acid at the temperature of 0 DEG C; and heating the obtained dark solution to 50 DEG C, keeping for 12 hours, then cooling to 20 DEG C, adding thionyl chloride and strong ammonia, stirring and diluting at the temperature of 0 DEG C, and drying to obtain target products. The preparation method has the advantages of stable reaction, stronger antimicrobial bactericidal effects of the target products than those of common antimicrobial drugs, easy enlarging production and no pollution in the production process.

Description

technical field [0001] The invention relates to a preparation method of 5,6-dihydro-6-methylthieno[2,3-b]thiopyran-2-sulfonamide-4-one. Background technique [0002] 5,6-dihydro-6-methylthieno[2,3-b]thiopyran-2-sulfonamide-4-one is an important pharmaceutical intermediate, which belongs to sulfonamide drugs and has strong Antibacterial pharmacological effects, so it has potential research and application value. There are not many studies on this compound abroad, and there is no complete preparation method for the synthesis of this organic compound; there is no report on its synthesis in China. In view of this fact, the present invention uses thiophene as a raw material to obtain the target product through a series of reactions. Contents of the invention [0003] The object of the present invention is to provide a kind of preparation method of 5,6-dihydro-6-methylthieno[2,3-b]thiopyran-2-sulfonamide-4-one, the preparation method is stable in reaction, easy to Scale up pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04A61P31/04
Inventor 谢宇胡金刚李明俊吴少林曾桂生魏娅
Owner 上饶京新药业有限公司
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