Preparation method of o-aminosulfonyl-benzoyl hydrazine

A technology of o-aminosulfonylbenzoyl hydrazide and aminosulfonylbenzoyl hydrazide, applied in the field of intermediate preparation of organic synthesis, can solve the problem that o-methoxycarbonylbenzenesulfonamide is not easy to obtain, the solvent is expensive, and the reaction steps are cumbersome and other problems, to achieve the effect of easy control, simple operation and high purity

Inactive Publication Date: 2010-06-16
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
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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...

Method used

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  • Preparation method of o-aminosulfonyl-benzoyl hydrazine

Examples

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Embodiment 1

[0023] This example is to illustrate the preparation method of o-aminosulfonylbenzohydrazide of the present invention.

[0024] (1) Suspend 1 mole of saccharin in 200 milliliters of absolute ethanol, and add 3 moles of 30% hydrazine hydrate dropwise under stirring at -5 to 5°C in an ice bath, and the addition is completed within 10 minutes;

[0025] (2) be warming up to reflux within 30 minutes; Continue reaction 5 hours under the reflux temperature;

[0026] (3) Transfer the reaction solution to a beaker, cool naturally to room temperature, let stand, and separate out granular white crystals, wash with water, wash with alcohol, and dry to obtain 0.65 moles of o-aminosulfonylbenzohydrazide of the present invention.

[0027] Test melting point: 195°C.

Embodiment 2

[0029] This example is to illustrate the preparation method of o-aminosulfonylbenzohydrazide of the present invention.

[0030] (1) Suspend 1 mole of saccharin in 200 milliliters of anhydrous methanol, and add 1 mole of 80% hydrazine hydrate dropwise under stirring under an ice-bath condition of -5 to 0°C, and the addition is completed within 10 minutes;

[0031] (2) Warming up to reflux in 30 minutes; Continue to react for 6 hours at the reflux temperature;

[0032] (3) The reaction solution was transferred to a beaker, cooled naturally to room temperature, left to stand, and granular white crystals were precipitated, washed with water, washed with alcohol, and dried to obtain 0.6 moles of o-aminosulfonylbenzohydrazide of the present invention.

Embodiment 3

[0034] This example is to illustrate the preparation method of o-aminosulfonylbenzohydrazide of the present invention.

[0035] (1) Take 1 mole of saccharin and suspend it in 200 milliliters of anhydrous isopropanol, and add 5 moles of 50% hydrazine hydrate dropwise under stirring under an ice bath condition of 0 to 5°C, under nitrogen protection, and complete the dropwise addition within 10 minutes;

[0036] (2) be warming up to reflux in 10 minutes; Continue reaction 15 hours under the reflux temperature;

[0037] (3) The reaction solution was transferred to a beaker, cooled naturally to room temperature, left to stand, and granular white crystals were precipitated, washed with water, washed with alcohol, and dried to obtain 0.7 moles of o-aminosulfonylbenzohydrazide of the present invention.

[0038] Test melting point: 195°C.

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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...

Claims

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Application Information

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IPC IPC(8): C07C311/16C07C303/36
Inventor 陈甫雪付占达
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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