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Synthetic method for sulfadiazine

A technique for the synthesis of sulfadiazine, which is applied in the field of organic chemical synthesis, can solve the problems of hindering the smooth progress of the condensation reaction, weakening the condensation efficiency of pyridine, and long condensation reaction time, etc., and achieves the effects of easy acquisition, high yield, and high product quality

Active Publication Date: 2016-01-20
HUNAN XIANGYIKANG PHARMA
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0013] Among the above synthetic routes, method (1) is more commonly used, but its raw material p-acetamidobenzenesulfonyl chloride is easily hydrolyzed, which increases the free acid in the reaction solution, weakens the pyridine condensation efficiency, and hinders the smooth progress of the entire condensation reaction. The requirements for the moisture content of raw materials and the dryness of equipment are relatively strict, and the condensation reaction time is long
Method (2) also has many problems. There are two steps of pressurized reaction in the synthesis method of propynyl alcohol as raw material, which has poor safety and high equipment investment; the boiling point of vinyl ether in the synthesis method of vinyl ether is low (36°C). , requires a huge refrigeration system, high power consumption, and poor safety

Method used

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  • Synthetic method for sulfadiazine
  • Synthetic method for sulfadiazine

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Experimental program
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Effect test

Embodiment 1

[0029] Embodiment 1: a kind of synthetic method of sulfadiazine comprises the following steps:

[0030] A will be 8.6gNH 4 Cl with 23.1g (NH 4 ) 2 CO 3 After mixing according to a certain ratio, add activated carbon catalyst, then add 32g of dicyandiamide and heat to melt, keep at 150°C for 30min;

[0031] B Add 80g of p-sulfamic acid to the above molten liquid, continue to melt 70g of sodium carbonate, raise the temperature to 150°C within 25min, and keep it for 30min;

[0032] C. Add 400ml of boiling water to the mixture obtained in step B. After stirring evenly, cool the obtained suspension to 40° C. and filter to obtain the crude sulfamidine.

[0033] Add 93g of 25% sodium methoxide methanol solution and 33g of crude sulfamidine to the flask in turn, add 13.5g of malondialdehyde under stirring, raise the temperature to 65°C, and react for 2h to complete the ring condensation reaction. After recovering methanol, the crude sulfadiazine is obtained. Add 200ml of water to...

Embodiment 2

[0034] Embodiment 2: a kind of synthetic method of sulfadiazine comprises the following steps:

[0035] A will be 8.6gNH 4 Cl with 30.9g (NH 4 ) 2 CO 3 After mixing according to a certain ratio, add activated carbon catalyst, then add 32g of dicyandiamide and heat to melt, and keep at 170°C for 30min;

[0036] B Add 80g of p-sulfamic acid to the above molten liquid, continue to melt 70g of sodium carbonate, raise the temperature to 150°C within 25min, and keep it for 30min;

[0037] C. Add 400ml of boiling water to the mixture obtained in step B. After stirring evenly, cool the obtained suspension to 40° C. and filter to obtain the crude sulfamidine.

[0038] Add 93g of 25% sodium methoxide methanol solution and 33g of crude sulfamidine to the flask in turn, add 12.0g of malondialdehyde under stirring, raise the temperature to 70°C, and react for 2.5h to complete the ring condensation reaction. After recovering methanol, crude sulfadiazine is obtained. Add 200ml of water ...

Embodiment 3

[0039] Embodiment 3: a kind of synthetic method of sulfadiazine comprises the following steps:

[0040] A will be 8.6gNH 4 Cl with 46.2g (NH 4 ) 2 CO 3 After mixing according to a certain ratio, add activated carbon catalyst, then add 32g of dicyandiamide and heat to melt, and keep at 180°C for 30min;

[0041]B Add 80g of p-sulfamic acid to the above molten liquid, continue to melt 70g of sodium carbonate, raise the temperature to 150°C within 25min, and keep it for 30min;

[0042] C. Add 400ml of boiling water to the mixture obtained in step B. After stirring evenly, cool the obtained suspension to 40° C. and filter to obtain the crude sulfamidine.

[0043] Add 100 g of 25% sodium methoxide methanol solution and 40 g of crude sulfadiazine to the flask in turn, add 14.5 g of malondialdehyde under stirring, raise the temperature to 60°C, and react for 4 hours to complete the ring condensation reaction. After recovering methanol, the crude sulfadiazine is obtained. Add 200m...

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Abstract

The invention discloses a synthetic method for sulfadiazine. The sulfadiazine is synthesized with sulphaguanidine and malonaldehyde as raw materials. The synthetic method has the advantages of being mild in reaction condition, short in reaction time, high in conversion rate and beneficial to industrial production.

Description

technical field [0001] The invention relates to a synthesis method of sulfadiazine, which belongs to the field of organic chemical synthesis. Background technique [0002] Sulfa drugs (sulfonamides; sulfadrugs) are synthetic anti-infective drugs with large output and variety, which occupy an important position in the development and production of drugs. In 1932, the discovery of 100 waves and more breaths created a new era of chemotherapy. In 1935, Trefonel and colleagues demonstrated that sulfonamides are the basic structures that produce antibacterial effects. Throughout the development of sulfa drugs, most of the sulfa drugs synthesized earlier have been eliminated, and only sulfadiazine is still used in clinical practice. Now it is mostly used to treat infections caused by sensitive bacteria and other sensitive pathogenic microorganisms. [0003] Sulfadiazine is white or off-white crystal or powder, odorless, tasteless, and gradually darkens when exposed to light. Sl...

Claims

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Application Information

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IPC IPC(8): C07D239/69
CPCC07D239/69
Inventor 帅放文王向峰章家伟
Owner HUNAN XIANGYIKANG PHARMA
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