2-Fluoroethyl bromide → 1-(2-Fluoroethyl)-5-nitro-1,3-dihydro-2h-2,1-benzisothiazole-2,2-dione
Reaktionsgleichung
C([O-])(O)=O.[Na+].[N+:6]([C:9]1[CH:10]=[CH:11][C:12]2[NH:16][S:15](=[O:18])(=[O:17])[CH2:14][C:13]=2[CH:19]=1)([O-:8])=[O:7].Br[CH2:21][CH2:22][F:23]>O>[F:23][CH2:22][CH2:21][N:16]1[C:12]2[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:19][C:13]=2[CH2:14][S:15]1(=[O:18])=[O:17]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
NaHCO3 (0.93 g, 11.0 mmol) is dissolved in H2O (15 mL) and 5-Nitro-1,3-dihydro-2H-2,1-benzisothiazole-2,2-dione (1) (1.90 g, 8.9 mmol) is added with stirring. The mixture is heated to 80° C. for 0.5 hrs and a yellow solid formed. The mixture is cooled to 0° C. and filtered. The solid is washed with cold H2O (15 mL) then with cold EtOH (25 mL). The yellow solid thus obtained is dried under high vacuum then dissolved in dry DMF (15 mL). 1-Bromo-2-fluoroethane (1.52 mL, 20.0 mmol) is added and the solution heated to 100° C. for 4 hrs. The solution is cooled to room temperature then poured into ice water (50 mL). The solid is collected by filtration and gave crystals (1.55 g, 67%) after recrystallization from EtOH. Mp 142-4° C. HRMS (FAB) calcd for C9H9FN2O4S +NA1 283.0165, found 283.0166.
Aufarbeitung
- customa yellow solid formed
- temperatureThe mixture is cooled to 0° C.
- filtrationfiltered
- washThe solid is washed with cold H2O (15 mL)
- customThe yellow solid thus obtained
- customis dried under high vacuum
- dissolutionthen dissolved in dry DMF (15 mL)
- temperaturethe solution heated to 100° C. for 4 hrs
- temperatureThe solution is cooled to room temperature
- filtrationThe solid is collected by filtration
Quellen und Nachweise
- ORD-Eintrag
- ord-694c4096000c4d0cbab2205b160e4118
- Quelldatensatz
- uspto-grants-2002_04
- Patentnummer
- US06365612B2
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