Sodium Hydroxide → Sertaconazole

HRID 1171917

Reaktionsgleichung

Reaktionsgleichung von HRID 1171917
[CH:1]1[CH:6]=[C:5]([Cl:7])[C:4]2[S:8][CH:9]=[C:10]([CH2:11][O:12][CH:13]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[CH2:14][N:15]3[CH:19]=[N:18][CH:17]=[CH:16]3)[C:3]=2[CH:2]=1.[N+]([O-])(O)=O.BrCC1C2C=CC=C(Cl)C=2SC=1.ClC1C=C(Cl)C=CC=1C(O)CN1C=CN=C1.[OH-].[Na+]>C1(C)C=CC=CC=1.O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1[CH:6]=[C:5]([Cl:7])[C:4]2[S:8][CH:9]=[C:10]([CH2:11][O:12][CH:13]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[CH2:14][N:15]3[CH:19]=[N:18][CH:17]=[CH:16]3)[C:3]=2[CH:2]=1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 200103Sertaconazole nitrateHCID 113799883-(Bromomethyl)-7-chloro-1-benzothiophene

Produkt 1

HCID 65863Sertaconazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 22272177Toluene waterLösungsmittel

Versuchsvorschrift

The specification CN 1358719 (CAPLUS 2003:711267) discloses the synthesis of sertaconazole mononitrate (I) by etherifying 3-bromomethyl-7-chlorobenzo[b]thiophene (III) with 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanol (II) at a molar ratio of 1:1 in toluene-water (3:1, v/v) in the presence of sodium hydroxide and 50% tetrabutylammonium chloride (IV, Z═Cl) solution at 80° C. for 4 hours, extracting with ethyl ether to obtain free base of sertaconazole, salifying with nitric acid and recrystallizing in 95% ethanol. The resulting content in sertaconazole mononitrate of the thus prepared product is >98.5%.

Aufarbeitung

  1. extractionextracting with ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7220f8852a7f442c812ae69241ac006e
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829726B2

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