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Preparation method of sulfadoxine

A technology of sulfadoxine and sulfadoxine sodium, which is applied in the field of preparation of sulfadoxine, can solve problems such as complex processes and quality, and achieve the effects of simple process operation, high yield and no production equipment.

Pending Publication Date: 2021-03-09
CHONGQING KANGLE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The technical problem to be solved by the present invention lies in a preparation method of sulfadoxine, which solves defects such as complex process and quality problems

Method used

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  • Preparation method of sulfadoxine
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  • Preparation method of sulfadoxine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Preparation of 4-chloro-5,6-dimethoxypyrimidine formula II

[0031] (see Bretschneider et al., Monatsh Chem. 96, 1661-1669 (1965))

[0032] Add 800g of methanol and 60g of sodium methoxide (1.11mol) into the reaction flask respectively, cool to 0°C~5°C, then add 179g (1.0mol) of 4,6-dichloro-5-methoxypyrimidine formula V, and keep at Stir and react at 0°C to 5°C for 1 hour, when the reaction is over, heat up to 20°C to 30°C, filter, transfer the filtrate to a reaction bottle, evaporate the solvent first, then add 1000g of water, extract three times with 1000g of dichloromethane, The organic layers were combined, the solvent was evaporated, and refined with ethyl acetate to obtain 4-chloro-5,6-dimethoxypyrimidine Formula II 162.5g as a white solid, with a yield of 93.0%.

Embodiment 2

[0033] The preparation of embodiment 2 sulfadoxine formula I (comparative experiment)

[0034] (See State Administration of Medicine. National Compilation of Raw Materials Processes, P172-175)

[0035] Add 200 g of methanol, 90 g (0.466 mol) of 28% sodium methoxide, and 50 g (0.159 mol) of condensate formula VI to the reaction flask in sequence, heat up to reflux for 4 hours, distill off methanol, and add water to distill off aqueous methanol. Use dilute acetic acid to adjust pH=10-11, add activated carbon for decolorization, filter, adjust the filtrate to pH=5.1-5.4 with dilute acetic acid, filter, wash, and dry to obtain sulfadoxin formula I124.5g, yield 80.2%; HPLC purity 98.0 %, of which the impurity of condensate formula VI is 0.6%

Embodiment 3

[0036] The preparation of embodiment 3 sulfadoxine formula I

[0037] Add DMF262g, sulfonamide sodium formula III97.1g (0.50mol), 4-chloro-5,6-dimethoxypyrimidine formula II87.3g (0.50mol), potassium carbonate 103.7g into the reaction flask, after adding Raise the temperature to 80°C-85°C and react for 2 hours. After the reaction, turn on the vacuum, and recover DMF by distillation under reduced pressure. After steaming, add water, stir until dissolved, adjust the pH to 7-8 with dilute acetic acid, cool, filter, and filter the cake Sulfonamide can be recovered.

[0038] Transfer the filtrate to another reaction flask, adjust pH=5.1-5.4 with dilute acetic acid, filter, wash, and dry to obtain sulfadoxine formula I141.5g, yield 91.2%; HPLC purity 99.8%, no condensate formula VI impurities .

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Abstract

The invention provides a preparation method of sulfadoxine. The method is a preparation method of sulfadimethoxine, and the sulfadimethoxine product is prepared by directly taking 4-chloro-5, 6-dimethoxypyrimidine and sodium sulfanilamide as raw materials through a condensation reaction. The method is simple in process, free of special requirements on equipment, simple and convenient to operate, good in product quality and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of sulfonamide antibacterial drugs, and in particular relates to a preparation method of sulfadoxine. Background technique [0002] Sulfadoxine, also known as sulfadoxine, English name: Sulfadoxine, chemical name: 4-(p-aminobenzenesulfonylamino)-5,6-dimethoxypyrimidine, CAS registration number: 2447-57- 6. [0003] The chemical structural formula is as follows: [0004] [0005] Sulfadoxine is a sulfonamide antibiotic. Sulfadoxine has the characteristics of long curative effect and low toxicity, and can treat general inflammations, such as upper respiratory tract infection pancreatitis, bacillary dysentery enteritis and skin infections, and has certain curative effect on the treatment of tuberculosis, lymphatic tuberculosis, etc. with other medicine compatibility. Can treat malaria. In addition, sulfadoxine can also be used as a preventive drug for rheumatic venereal diseases. [0006]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/69
CPCC07D239/69
Inventor 张金生蔡中文谢晓芹王静沈文晖
Owner CHONGQING KANGLE PHARMA
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