Butoconazole (trade names Gynazole-1, Mycelex-3) is an

imidazole Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non ...

antifungal An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as ...

used in

gynecology Gynaecology or gynecology (see American and British English spelling differences, spelling differences) is the area of medicine that involves the treatment of women's diseases, especially those of the reproductive organs. It is often paired with ...

. It is administered as a vaginal cream.Butoconazole

Synthesis

Reaction of

epichlorohydrin Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organ ...

with 4-Chlorobenzyl magnesium bromide leads to 1-chloro-4-(4-chlorophenyl)butan-2-ol (3). Displacement with sodium imidazole, conversion of the secondary alcohol to the chloride (

SOCl2 Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately Volatility (chemistry), volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a Halogenation, chlorinating reagen ...

), and displacement with 2,6-dichlorobenzenethiol concludes the synthesis of the antifungal butoconazole.

References

External links

* Chloroarenes Thioethers Imidazole antifungals Lanosterol 14α-demethylase inhibitors {{antimicrobial-stub