Water → 3-Amino-4-isopropoxy-benzenesulfonamide
Reaktionsgleichung
[BH4-].[Na+].[CH:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:9][C:8]=1[N+:17]([O-])=O)([CH3:5])[CH3:4].O>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:17][C:8]1[CH:9]=[C:10]([S:13]([NH2:16])(=[O:14])=[O:15])[CH:11]=[CH:12][C:7]=1[O:6][CH:3]([CH3:5])[CH3:4]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 23 °C
Versuchsvorschrift
Sodium borohydride (1.88 g, 49.6 mmol) was added slowly to a solution of nickel (II) chloride hexahydrate (3.93 g, 16.5 mmol) in methanol (60 mL) at 0° C. and the resulting black suspension was stirred for 30 min at 23° C. The mixture was cooled to 0° C. and 4-isopropoxy-3-nitro-benzenesulfonamide (8.6 g, 33.0 mmol, example 2, step c) was added followed by sodium borohydride (4.38 g, 115.6 mmol). The resulting black suspension was stirred for 30 min at 23° C. Water was added to the reaction mixture to quench excess NaBH4, followed by addition of saturated aqueous NaHCO3. The product was extracted with dichloromethane and the organic phase was washed with brine, dried with Na2SO4 and evaporated to give the title compound.
Aufarbeitung
- temperatureThe mixture was cooled to 0° C.
- stirringThe resulting black suspension was stirred for 30 min at 23° C
- customto quench excess NaBH4
- additionfollowed by addition of saturated aqueous NaHCO3
- extractionThe product was extracted with dichloromethane
- washthe organic phase was washed with brine
- dry with materialdried with Na2SO4
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-0208af1266e342db8483b4ef773e0e50
- Quelldatensatz
- uspto-grants-2014_11
- Patentnummer
- US08883473B2
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