Reaktion #64467

Reaktionsgleichung

H2O

5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

sodium hydride

isopropyl iodide

→

title compound

Ausbeute 48.4%

5-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2,4-dihydro-2-isopropyl-3H-1,2,4-triazol-3-one

Ausbeute 48.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe orange mixture was stirred at room temperature overnight
2. 2
   Extraktionextracted 4× with ethyl acetate
3. 3
   WaschenThe combined organic fractions were washed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   EinengenThe filtrate was concentrated in vacuo
7. 7
   Sonstigechromatographed twice on silica gel (elution with 1.5% MeOH in CH2Cl2)

Vorschrift

To a suspension of 54 mg (1.35 mmole) of sodium hydride (60% in oil) in 1 ml of dry DMF was added 200 mg (0.452 mmole) of 5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step G). The resulting mixture was stirred under N2 at room temperature for 2 hours. Then 270 μL (460 mg, 2.70 mmole) of isopropyl iodide was added dropwise, and the orange mixture was stirred at room temperature overnight. Next, the mixture was treated with H2O and extracted 4× with ethyl acetate. The combined organic fractions were washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo, and the residue was flash chromatographed twice on silica gel (elution with 1.5% MeOH in CH2Cl2) to yield 106 mg (48%) of the title compound; satisfactory purity by TLC in 98.5:1.5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 485 (M+1)+.

Quelle