ChemicalBook--->CAS DataBase List--->99592-32-2

99592-32-2

99592-32-2 Structure

99592-32-2 Structure
IdentificationMore
[Name]

Sertaconazole nitrate
[CAS]

99592-32-2
[Synonyms]

1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole nitrate
7-CHLORO-3-[1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)ETHOXY-METHYL] BENZO[B]THIOPHENE NITRATE
SERTACONAZOLE
SERTACONAZOLE NITRATE
1-(2-((7-chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1h-i
1h-imidazole,1-(2-((7-chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl)
7-chloro-3-(1-(2,4-dichlorophenyl)-2-(1h-imidazol-1-yl)ethoxy-methyl)benzo(b
7-cloro-3-(1-(2,4-diclorofenil)-2-(1h-imidazol-1-il)etoxi-metil)benzo(b)tiof
eno
fi-7045
Sertaconazole nitrate
1-[2-[(7-Chlorobenzo[b]thien-3-y1)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
Dermofix
FI-7056
Zalain
1-[2-[(7-Chlorobenzo[b]thiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
1-[β-[(7-Chlorobenzo[b]thiophene-3-yl)methoxy]-2,4-dichlorophenethyl]-1H-imidazole
[EINECS(EC#)]

1312995-182-4
[Molecular Formula]

C20H15Cl3N2OS
[MDL Number]

MFCD00868881
[Molecular Weight]

437.77
[MOL File]

99592-32-2.mol
Chemical PropertiesBack Directory
[Melting point ]

146-147°
[Boiling point ]

614.1±55.0 °C(Predicted)
[density ]

1.43±0.1 g/cm3(Predicted)
[storage temp. ]

Refrigerator
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

6.68±0.12(Predicted)
[color ]

White to Pale Yellow
[CAS DataBase Reference]

99592-32-2(CAS DataBase Reference)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium hydride-->Silica gel-->Thianaphthene-->Hexamethylphosphoramide
Hazard InformationBack Directory
[Description]

Sertaconazole has been developed and launched for the treatment of dermatological fungal infections by Ferrer Internacional S. A. Mylan received FDA approval for sertaconazole nitrate cream for the treatment of athlete's foot (tinea pedis) at the end of 2003.
[Uses]

An imidazole antifungal agent, inhibits the synthesis of ergosterol, an essential cell wall component of fungi.
[Definition]

ChEBI: 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that carries a 2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl group at position 1. It is a dichlorobenzene, an ether, a member of imidazoles and a member of 1-benzothiophenes.
[Synthesis]

2,4-Dichloro acetophenone 169 was brominated at low temperature to give bromide intermediate 170, which was used without isolation. To the same pot, five-fold excess of imidazole was added to give imidazolylacetophenone 171 in 71% yield from 169. Sodium borohydride was employed to reduce ketone 171 to alcohol 172 in 78% yield. Racemic alcohol 172 was resolved with (-)-DIP-chloride to give its corresponding chiral R-alcohol 173 in 80% yield. Compound 173 was then alkylated with 3-bromomethyl-7-chlorobenzo[b]thiophene (174) in dry DMF in the presence of potassium t-butoxide to give the alkylation product in 68% yield. Finally, 60% nitric acid was used to make sertaconazole mononitrate (XXI) in 89% yield.

Synthesis_99592-32-2

Spectrum DetailBack Directory
[Spectrum Detail]

Sertaconazole nitrate(99592-32-2)1HNMR
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