Reaktionsgleichung
[N+:1]([O-:4])(O)=[O:2].OS(O)(=O)=O.[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[CH:21]1([NH2:24])[CH2:23][CH2:22]1.CCN(C(C)C)C(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[CH:21]1([NH:24][S:17]([C:14]2[CH:15]=[CH:16][C:11]([F:10])=[C:12]([N+:1]([O-:4])=[O:2])[CH:13]=2)(=[O:19])=[O:18])[CH2:23][CH2:22]1Komponenten
Versuchsvorschrift
To a solution of fuming nitric acid (8 mL) and conc. H2SO4 (16 mL), was added 4-fluorobenzenesulfonyl chloride (1.3 g, 6.7 mmol) in small portions. The mixture was stirred at RT for 2 h. and then poured onto crushed ice (60 g) and extracted with dichloromethane (2×). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was dissolved in CH2Cl2 (30 mL) cooled to −40° C. and cyclopropylamine (388 mg, 6.8 mmol), followed by DIPEA (8 mmol) were added. After stirring at −40° C. for 2 h, the mixture was poured on 5% citric acid solution and extracted with dichloromethane. The organic layer was separated, and passed through a short pad of silica gel and concentrated in vacuo to afford N-cyclopropyl-4-fluoro-3-nitrobenzenesulfonamide (1.6 g, 92%) as a yellow solid.
Aufarbeitung
- additionpoured
- extractionextracted with dichloromethane (2×)
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- dissolutionThe residue was dissolved in CH2Cl2 (30 mL)
- temperaturecooled to −40° C.
- additionwere added
- stirringAfter stirring at −40° C. for 2 h
- extractionextracted with dichloromethane
- customThe organic layer was separated
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-462377d8589748f69115599778a6a316
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07084160B2
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