반응 #64467

반응 방정식

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

수율 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

수율 48.4%

용매

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGthe orange mixture was stirred at room temperature overnight
2. 2
   추출extracted 4× with ethyl acetate
3. 3
   세척The combined organic fractions were washed with brine
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축The filtrate was concentrated in vacuo
7. 7
   기타chromatographed twice on silica gel (elution with 1.5% MeOH in CH2Cl2)

실험 절차

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)+.

출처