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Preparation method of broad-spectrum antifungal drug fluconazole
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A drug fluconazole, antifungal technology, applied in the field of preparation of broad-spectrum antifungal drug fluconazole, can solve the problems of high production cost, low product yield, poor product quality, etc., and achieve simple operation, low price, The effect of reducing production costs
Inactive Publication Date: 2012-02-08
ZHEJIANG GENEBEST PHARMA
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[0005] The purpose of the present invention is to solve the problems of high production cost, low product yield and poor product quality in the prior art, and provide a preparation method of broad-spectrum antifungal drug fluconazole, which has low production cost and no production equipment. Special requirements, mild reaction conditions, easy operation and no damage to the environment, suitable for industrialization
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Embodiment 1
[0026] (1) Preparation of 1-(hydroxymethyl)-1H-1,2,4-triazole
[0027] Add 1H-1,2,4-triazole (69g, 1mol), 1,2-dichloroethane (270ml) and catalyst triethylamine (6.9g) into the reactor, stir well, add polymerFormaldehyde (33g, 1.1mol), then continue to stir and heat up to reflux reaction for about 6 hours, then cool to room temperature, filter and collect the precipitated solid, and dry to obtain a white solid, namely 1-(hydroxymethyl)-1H-1 , 2,4-triazole, about 92.3g, yield about 93.2%. M.P.65-67°C. 1H-NMR (CDCl3, 500MHz) δ: 8.59(s, 1H), 8.07(s, 1H), 7.28(s, 1H), 5.75(s, 2H).
[0028] (2) Preparation of 1-(chloromethyl)-1H-1,2,4-triazole
[0029] Add 1-(hydroxymethyl)-1H-1,2,4-triazole (99g, 1mol) and 1,2-dichloroethane (1000ml) into the reactor, stir and dissolve, then use ice-salt bath Cool down to about 5°C, then add thionylchloride (595g, 5mol) dropwise, and keep stirring the reaction mixture during the dropwise addition, control the rate of addition so that the reac...
Embodiment 2
[0034] The other steps of this example are the same as in Example 1, the difference lies in the preparation of 1-(hydroxymethyl)-1H-1,2,4-triazole in step (1):
[0035] Add 1H-1,2,4-triazole (69g, 1mol), 1,2-dichloroethane (220ml) and catalyst triethylamine (6.9g) into the reactor, stir well, add polymerFormaldehyde (30g, 1.0mol), then continue to stir and heat up to reflux reaction for 4 hours, then cool to room temperature, filter and collect the precipitated solid, and dry to obtain a white solid, that is, 1-(hydroxymethyl)-1H-1, 2,4-triazole, about 88.3g, yield about 89.2%. M.P.65-67°C. 1H-NMR (CDCl3, 500MHz) δ: 8.59(s, 1H), 8.07(s, 1H), 7.28(s, 1H), 5.75(s, 2H).
Embodiment 3
[0037] The other steps of this example are the same as in Example 1, the difference lies in the preparation of 1-(hydroxymethyl)-1H-1,2,4-triazole in step (1):
[0038] Add 1H-1,2,4-triazole (69g, 1mol), 1,2-dichloroethane (250ml) and catalyst triethylamine (6.9g) into the reactor, stir well, add polymerFormaldehyde (32g, 1.07mol), then continue to stir and heat up to reflux reaction for about 6 hours, then cool to room temperature, filter and collect the precipitated solid, and dry to obtain a white solid, namely 1-(hydroxymethyl)-1H-1 , 2,4-triazole, about 91.1g, yield about 92.0%. M.P.65-67°C. 1H-NMR (CDCl3, 500MHz) δ: 8.59(s, 1H), 8.07(s, 1H), 7.28(s, 1H), 5.75(s, 2H).
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Abstract
The invention discloses a preparation method of a broad-spectrum antifungaldrugfluconazole, and aims to solve the problems of high production cost, low product yield and poor product quality in the prior art. The method comprises the following steps of: carrying out an addition reaction on 1H-1,2,4-triazole, which serves as the raw material, and polyformaldehyde to obtain 1-(hydroxymethyl)-1H-1,2,4-triazole; carrying out a chlorination reaction on the 1-(hydroxymethyl)-1H-1,2,4-triazole and thionylchloride to obtain 1-(chloromethyl)-1H-1,2,4-triazole; and finally, after the 1-(chloromethyl)-1H-1,2,4-triazole and magnesium form a Grignard reagent, reacting with ethyl 2,4-difluorobenzoate to obtain the fluconazole. By using the domestically common and accessible compound as the raw material, the invention has the advantages of low production cost, no special requirements for production equipment, mild reaction conditions and no environmental pollution, and is simple to operate and suitable for industrial popularization.
Description
technical field [0001] The invention relates to a preparation method of a broad-spectrum antifungaldrugfluconazole, in particular to a preparation method of a broad-spectrum antifungaldrug fluconazole. Background technique [0002] Fungal infection is a common disease, generally divided into superficial infection and deep fungal infection, wherein the deep fungal infection is very harmful, serious can cause death. Antifungal drugs are mainly azoles, of which fluconazole was approved by the FDA in 1990 and launched in the United States. Over the past two decades, this drug has been listed in more than 30 countries around the world, and has been firmly in the leading position in the antifungal drug market. Its curative effect And the scope of application has been affirmed by the majority of patients. Therefore, improving its production process, reducing its production cost, expanding its promotion scope, and benefiting more patients have become the focus of research workers...
Claims
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