2-Aminopyridine → 6-Aminopyridine-3-sulfonyl chloride
Reaktionsgleichung
[Cl:1][S:2]([OH:5])(=O)=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.S(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>>[NH2:6][C:7]1[N:8]=[CH:9][C:10]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:11][CH:12]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
To 123.8 g (1.06 mol) of chlorosulfonic acid was added 10.00 g (0.106 mol) of 2-aminopyridine by portions under ice-cooling. Thionyl chloride (50.56 g, 0.425 mol) was added thereto, followed by heating under reflux for 2.5 hours and further stirring at 150° C. for 7 hours. The reaction solution was poured onto ice water, neutralized by adding sodium bicarbonate thereto and extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution, water and brine successively, dried over magnesium sulfate and then concentrated to dryness. The resulting residue was suspended in ethyl ether and the insoluble matters were filtered off. The filtrate was concentrated to dryness and the resulting residue was recrystallized from ethyl ether-hexane to give 6.58 g of the title compound.
Aufarbeitung
- temperaturecooling
- temperatureby heating
- temperatureunder reflux for 2.5 hours
- additionThe reaction solution was poured onto ice water
- extractionextracted with ethyl acetate
- washThe organic layer was washed with a saturated sodium bicarbonate solution, water and brine successively
- dry with materialdried over magnesium sulfate
- concentrationconcentrated to dryness
- filtrationthe insoluble matters were filtered off
- concentrationThe filtrate was concentrated to dryness
- customthe resulting residue was recrystallized from ethyl ether-hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-52391d3dc36c47c1b76a25521b0e5e31
- Quelldatensatz
- uspto-grants-2004_01
- Patentnummer
- US06673787B2
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