SULCONAZOLE

SULCONAZOLEсульконазол , سولكونازول , 硫康唑

• Molecular FormulaC₁₈H₁₅Cl₃N₂S
• Average mass397.749 Da

1H-Imidazole, 1-[2-[[(4-chlorophenyl)methyl]thio]-2-(2,4-dichlorophenyl)ethyl]- [ACD/Index Name] 
4332
5D9HAA5Q5S
61318-90-9[RN]
(±)-1-[2,4-Dichloro-b-[(p-chlorobenzyl)thio]phenethyl]imidazole
1-[2-[[(4-Chlorophenyl)methyl]thio]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole: SulconazoleCAS Registry Number: 61318-90-9 
CAS Name: 1-[2-[[(4-Chlorophenyl)methyl]thio]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole 
Additional Names: (±)-1-[2,4-dichloro-b-[(p-chlorobenzyl)thio]phenethyl]imidazole 
Molecular Formula: C18H15Cl3N2S 
Molecular Weight: 397.75 
Percent Composition: C 54.35%, H 3.80%, Cl 26.74%, N 7.04%, S 8.06% 
Literature References: Prepn: K. A. M. Walker, DE2541833; idem,US4055652 (1976, 1977 both to Syntex). HPLC determn in plasma: M. Fass et al.,J. Pharm. Sci.70, 1338 (1981). Mechanism of action study: W. H. Beggs, Biochem. Arch.10, 117 (1994). Clinical trial in tinea pedis: W. A. Akers et al.,J. Am. Acad. Dermatol.21, 686 (1989). Review of pharmacology and clinical efficacy: P. Benfield, S. P. Clissold, Drugs35, 143-153 (1988). 
Derivative Type: Nitrate 
CAS Registry Number: 61318-91-0 
Manufacturers’ Codes: RS-44872 
Trademarks: Exelderm (Syntex); Myk (Cassenne); Sulcosyn (Syntex) 
Molecular Formula: C18H15Cl3N2S.HNO3 
Molecular Weight: 460.76 
Percent Composition: C 46.92%, H 3.50%, Cl 23.08%, N 9.12%, S 6.96%, O 10.42% 
Properties: Colorless crystals from acetone, mp 130.5-132°. 
Melting point: mp 130.5-132° 
Therap-Cat: Antifungal. 
Keywords: Antifungal (Synthetic); Imidazoles.

Sulconazole (trade name Exelderm) is an antifungal medication of the imidazole class. It is available as a cream or solution to treat skin infections such as athlete’s foot, ringworm, jock itch, and sun fungus.^[1][2] Although not used commercially for insect control, sulconazole nitrate exhibits a strong anti-feeding effect on the keratin-digesting Australian carpet beetle larvae Anthrenocerus australis.^[3]

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DE 2541833 US 4038409

(Read example 5 and 9 in US patent.)

https://patents.google.com/patent/US4038409A/en

EXAMPLE 5Alternative Route to 1-[β-(R-carbonylthio)phenethyl]imidazolesA. Preparation of 1-[2,4-dichloro-β-(methylcarbonylthio)-phenethyl]imidazole, oxalate.1-(β,2,4-Trichlorophenethylimidazole (1.19g) in 5 ml of dry tetrahydrofuran was added to preformed sodium thioacetate, generated in situ from 720 mg thioacetic acid and sodium hydride (480 mg 57% dispersion in mineral oil) in 20 ml. tetrahydrofuran and the mixture stirred and refluxed under nitrogen for 18 hours. The solvent was removed under reduced pressure, water (20 ml) added and the product extracted with ether. The extracts were washed with water, dried (MgSO₄), evaporated and the residue chromatographed on silica gel eluting with 10-20% acetone in dichloromethane. The pure product in ether was treated dropwise with ethereal oxalic acid until precipitation was complete, and the thus obtained oxalate salt of 1-[2,4-dichloro-β-(methylcarbonylthio)phenethyl]imidazole recrystallized from acetone/ethyl acetate with mpBy substituting other available sodium thioacids for sodium thioacetate, other compounds of this invention may be prepared.

EXAMPLE 9A. Preparation of 1-[2,4-dichloro-β-(4-chlorobenzylthio)-phenethyl]imidazoleTo a stirred solution of 330 mg sodium hydroxide in 30 ml methanol under nitrogen is added 810 mg of 1-[2,4-dichloro-β-(methylcarbonylthio)phenethyl]imidazole oxalate and the mixture is stirred at room temperature for ca. 30 minutes (until thin layer chromatography shows the disappearance of the ester). α,p-dichlorotoluene (350 mg) is then added, the solution stirred a further 15 minutes and the solvent removed under reduced pressure. Ether and water are then added to the residue and the ether extract washed with water, dried (MgSO₄) and concentrated. Dropwise addition of nitric acid (d = 1.42) until precipitation is complete gives the nitrate salt of 1-[2,4-dichloro-β-(4-chlorobenzylthio)phenethyl]imidazole, recrystallized from acetone, mp 130.5°-132° C.B. By using other compounds of this invention exemplified by those set forth in Examples 2 and 4 and other suitable (substituted) hydrocarbyl halides (or mesylates, tosylates), other compounds may be prepared.

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https://www.sciencedirect.com/science/article/pii/S2095177917301405

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Synthesis Path

Substances Referenced in Synthesis Path

References

1. ^ Drugs.com: sulconazole topical
2. ^ Fromtling RA (April 1988). “Overview of medically important antifungal azole derivatives”. Clinical Microbiology Reviews. 1 (2): 187–217. doi:10.1128/CMR.1.2.187. PMC 358042. PMID 3069196.
3. ^ Sunderland MR, Cruickshank RH, Leighs SJ (2014). “The efficacy of antifungal azole and antiprotozoal compounds in protection of wool from keratin-digesting insect larvae”. Textile Research Journal. 84 (9): 924–931. doi:10.1177/0040517513515312.

/////////SULCONAZOLE, сульконазол , سولكونازول , 硫康唑 ,  Antifungal, 

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