Preparation method of o-aminosulfonyl-benzoyl hydrazine

Abstract

The invention relates to a preparation method of pharmaceutical intermediates, in particular to a preparation method of o-aminosulfonyl-benzoyl hydrazine, belonging to the intermediates preparation field of organic synthesis. The preparation method comprises the following steps of: (1), firstly, determining that the feed ratio of o-sulfonylbenzoylimine to hydrazine hydrate is 1mol to 1-10mol; at the room temperature, adding the o-sulfonylbenzoylimine to a container, adding anhydrous alcohol as a solvent, and stirring to fully mix; and under the ice-bath condition of 5 DEG C below zero-5 DEG C, dropwise adding the hydrazine hydrate while stirring; (2), heating the solution to back flow within 30 minutes when the solution changes clear; and continuously reacting for 1-15 hours at the backflow temperature; and (3), transferring the reaction liquid to a beaker for naturally cooling to the room temperature, standing to separate out granulous white crystals, washing with water and alcohol, and drying to obtain the final product, i.e. o-aminosulfonyl-benzoyl hydrazine. In the invention, the preparation method has the advantages of simple operation, easy control, one-step finished reaction, high purity, innocuity and the like.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of o-aminosulfonylbenzohydrazide, and belongs to the field of intermediate preparation of organic synthesis. Background technique [0002] O-aminosulfonylbenzohydrazide is an important intermediate in organic synthesis, mainly used in pharmaceutical intermediates, organic synthesis, organic solvents, and can also be used in the production of dyes, pesticides and spices. [0003] When synthesizing o-aminosulfonylbenzohydrazide, the general reaction steps are cumbersome, or a large amount of toxic and harmful substances are directly contacted during the synthesis process, which causes great pollution to the environment. In 1960, Calvert utilized hydrazine hydrate and saccharin in a dioxane solvent to synthesize o-sulfamoylbenzoyl hydrazide, but the solvent used was expensive (The Journal of Organic Chemistry, 1960, 25 (3), 413-416. ); In...

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Problems solved by technology

[0003] When synthesizing o-aminosulfonylbenzohydrazide, the general reaction steps are cumbersome, or a large amount of toxic and harmful substances are directly exposed to during the synthesis process, and cause great pollution to the environment

In 1960, Calvert utilized hydrazine hydrate and saccharin in a dioxane solvent to synthesize o-sulfamoylbenzoyl hydrazide, but the solvent used was expensive (The Journal of Organic Chemistry, 1960, 25 (3), 413-416. ); In 2005, Winumzai utilized o-methoxycarbonylbenzenesulfonamide and hydrazine hydrate to synthesize o-aminosulfonylbenzoyl hydrazide in methanol, but the shortcoming of this method is that o-methoxycarbonylbenzenesulfonamide is not easy to obtain (Journal of Medicinal Chemistry, 2005, 48 (6), 2121-2125.); In 2007, Wang Shuyan of Tianjin University first synthesized o-methoxycarbonylbenzenesulfonamide under the conditions of methanol and concentrated hydrochloric acid, and then synthesized o-methoxycarbonylbenzenesulfonamide under the conditions of ethanol and hydrazine hydrate. Aminosulfonyl benzoyl hydrazide (Tianjin University, Wang Shuyan, 2007, doctoral dissertation), its shortcoming is that reaction steps are loaded down with trivial details

[0004] At present, the use of saccharin in alcohol as a solvent and hydrazine hydrate to produce o-aminosulfonylbenzohydrazide has not been reported at home and abroad.

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