Nitric Acid → HCID 14819589, Verbindung
Reaktionsgleichung
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:3][CH2:2]1.[N+:17]([O-])([OH:19])=[O:18]>CCOC(C)=O>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[C:10]([N+:17]([O-:19])=[O:18])[CH:9]=[CH:8][C:7]=2[NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:2][CH2:3]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
N-(2-(cyclopropylmethoxy)phenyl)methanesulfonamide (1.3 g, 5.39 mmol) was cooled to 0° C., and nitric acid (0.746 ml, 10.77 mmol) was added. The mixture was stirred at RT for 1 hour. The mixture was diluted with EtOAc and washed with NaHCO3 5% and brine. The organic phase was dried over Na2SO4, and the solvent was removed. The crude was purified by flash chromatography on silica gel cartridge (petroleum ether:EtOAc=80:20 to 60:40). 0.390 g of title product were obtained by collection and evaporation of clean fractions. Product obtained from mixed fractions was triturated with EtOAc affording 0.285 g of title compound. The mother liquor from trituration was evaporated and purified by flash chromatography on silica gel (DCM:petroleum ether=80:20) to give 0.155 g of title compound. Title product N-(2-(cyclopropylmethoxy)-4-nitrophenyl)-methanesulfonamide was obtained (0.830 g, 2.90 mmol, 53.8% yield, MS/ESI+ 286.9 [MH]+).