Reaktion #215757

Reaktionsgleichung

sulfur dioxide

n-Butyllithium

sodium acetate trihydrate

hydroxylamine-O-sulfonic acid

product

6-Chloro-4-methyl-2H-thieno[3,2-e]-1,2,3-thiadiazine 1,1-dioxide

→

4-Methyl-2H-thieno[3,2-e]-1,2,3-thiadiazine-6-sulfonamide 1,1-dioxide

Lösungsmittel

water

—

hexanes

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   SonstigeEvaporation of the volatiles
3. 3
   Sonstigeprovided a residue which
4. 4
   TemperaturThis solution was cooled to 0° C.
5. 5
   ExtraktionThe reaction mixture was extracted with ethyl acetate (2×50 mL)
6. 6
   TrocknenThe combined extracts were dried over MgSO4
7. 7
   Einengenconcentrated to a crude oil which
8. 8
   Sonstigewas purified by flash column chromatography (silica, hexane-ethyl acetate gradient)
9. 9
   Sonstige>163° C

Vorschrift

The product from step A (1.5 g, 6.30 mmol) was dissolved in dry THF (60 mL) and cooled to -78° C. under nitrogen. n-Butyllithium (5.33 mL of a 2.5 M solution in hexanes, 13.3 mmol) was added dropwise and the mixture was stirred for 1h at -78° C. A stream of sulfur dioxide gas was passed through the surface of the mixture for 15 min and then the mixture was allowed to warm to room temperature. Evaporation of the volatiles provided a residue which was dissolved in water (60 mL) to which was added sodium acetate trihydrate (2.59 g, 19.06 mmol). This solution was cooled to 0° C. and hydroxylamine-O-sulfonic acid (2.15 g, 19.06 mmol) was added followed by stirring for 18h. The reaction mixture was extracted with ethyl acetate (2×50 mL). The combined extracts were dried over MgSO4 and concentrated to a crude oil which was purified by flash column chromatography (silica, hexane-ethyl acetate gradient) to lead to a white solid (1 g, 50%). decomposition: >163° C. 1H NMR (DMSO-d6): δ:2.48 (3H, 1s, CH3); 8.17 (2H, s, NH2 exchangeable).

Quelle