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Preparation method of o-aminosulfonyl-benzoyl hydrazine

A technology of o-aminosulfonylbenzohydrazide and aminosulfonylbenzohydrazide, which is applied in the field of intermediate preparation of organic synthesis, and achieves the effects of simple operation, high purity and simple purification

Inactive Publication Date: 2013-02-13
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[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.

Method used

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  • Preparation method of o-aminosulfonyl-benzoyl hydrazine
  • Preparation method of o-aminosulfonyl-benzoyl hydrazine

Examples

Experimental program
Comparison scheme
Effect test

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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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/16C07C303/36
Inventor 陈甫雪付占达
Owner BEIJING INSTITUTE OF TECHNOLOGYGY