Synthesis method for 4-sulfonamidophenylhydrazine hydrochloride

A technology of hydrazinobenzenesulfonamide and aminobenzenesulfonamide is applied in the field of synthesizing celecoxib intermediates to achieve the effects of inhibiting decomposition, accurately controlling reaction temperature and stably producing

Inactive Publication Date: 2018-01-12
HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] In order to solve the various difficulties mentioned above, the technical problem to be solved in the present invention is to provide a kind of intrinsically safe, continuous, stable, high-yield and high-purity p-hydrazinobenzenesulfonamide hydrochloride synthesis technology

Method used

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  • Synthesis method for 4-sulfonamidophenylhydrazine hydrochloride
  • Synthesis method for 4-sulfonamidophenylhydrazine hydrochloride
  • Synthesis method for 4-sulfonamidophenylhydrazine hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0040]Weigh 80g of p-aminobenzenesulfonamide and add it to 800ml of water, then add 50ml of concentrated hydrochloric acid and stir to dissolve it as material I, weigh 32g of sodium nitrite and dissolve it in 500ml of water as material II, weigh 220g of stannous chloride and dissolve it with 800ml In the concentrated hydrochloric acid as material III, control metering pump A to make the flow rate of material I be 16ml / min, control metering pump B to make the flow rate of material II be 10ml / min, control metering pump C to make the flow rate of material III be 16ml / min, The mol ratio of sodium nitrite and p-aminobenzenesulfonamide is 1:1, the mol ratio of stannous chloride and p-sulfanilamide is 2.5:1, the residence time of diazotization reaction is 56 seconds, and the diazonium salt reduction The residence time of the reaction is 41 seconds, the reaction temperature of temperature zone I is 0°C, and the reaction temperature of temperature zone II is -10°C, collect the reaction ...

Embodiment 2

[0042] Weigh 100g of p-aminobenzenesulfonamide and add it to 800ml of water, then add 50ml of concentrated hydrochloric acid and stir to dissolve it as material I, weigh 40g of sodium nitrite and dissolve it in 500ml of water as material II, weigh 300g of stannous chloride and dissolve it with 1000ml In the concentrated hydrochloric acid as material III, control metering pump A to make the flow velocity of material I be 16ml / min, control metering pump B to make the flow velocity of material II be 9ml / min, control metering pump C to make the flow velocity of material III be 18ml / min, The mol ratio of sodium nitrite and sulfanilamide is 1:1, the mol ratio of stannous chloride and sulfanilamide is 3.0:1, the residence time of diazotization reaction is 58 seconds, and the diazonium salt reduction The residence time of the reaction is 34 seconds, the reaction temperature in temperature zone I is -5°C, and the reaction temperature in temperature zone II is -20°C, collect the reaction...

Embodiment 3

[0044] Weigh 80g of sulfanilamide and add it to 800ml of water, then add 40ml of concentrated hydrochloric acid and stir to dissolve it as material I, weigh 32g of sodium nitrite and dissolve it in 500ml of water as material II, weigh 220g of stannous chloride and dissolve it with 800ml In the concentrated hydrochloric acid as material III, control metering pump A to make the flow velocity of material I be 20ml / min, control metering pump B to make the flow velocity of material II be 12ml / min, control metering pump C to make the flow velocity of material III be 20ml / min, The mol ratio of sodium nitrite and p-aminobenzenesulfonamide is 1:1, the mol ratio of stannous chloride and p-sulfanilamide is 2.5:1, the residence time of diazotization reaction is 50 seconds, and the diazonium salt reduction The residence time of the reaction is 28 seconds, the reaction temperature of temperature zone I is 0°C, and the reaction temperature of temperature zone II is -5°C, collect the reaction ...

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Abstract

The invention discloses a synthesis method for 4-sulfonamidophenylhydrazine hydrochloride, which relates to the field of organic synthesis. The method includes the following steps: p-aminobenzenesulfonamide is dissolved in diluted hydrochloric acid to serve as a material I, sodium nitrite is dissolved in water to serve as a material II, stannous chloride is dissolved in concentrated hydrochloric acid to serve as a material III, and the material I and the material II undergo diazotization reaction after being preheated, so that diazonium salt is produced; the product and the material III undergo diazonium salt reduction reaction, and after processing, 4-sulfonamidophenylhydrazine hydrochloride is obtained. The method provided by the invention is safe and environmentally friendly, and the method remarkably increases yield and product purity in comparison with conventional methods.

Description

technical field [0001] The invention belongs to the field of synthesizing drugs for osteoarthritis and rheumatoid arthritis in organic synthesis, and in particular relates to a method for synthesizing celecoxib intermediates. Background technique [0002] The chemical name of celecoxib is 4-{5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl}benzenesulfonamide, which was developed by GD Searle Company of the United States. First launched in the United States in 1998, it is the first type II cyclooxygenase (COX-2) inhibitor to be marketed. It is clinically used for the treatment of inflammations such as osteoarthritis and rheumatoid arthritis. Its chemical structure is as follows: [0003] [0004] The synthesis of celecoxib in the current literature mainly consists of the following methods: [0005] method one: [0006] [0007] The β-diketone intermediate is obtained by claimen condensation of p-methylacetophenone and ethyl trifluoroacetate under alkaline condi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/40C07C311/37B01J19/00
Inventor 任吉秋杨昆李海涛
Owner HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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