Reacción #215755

Ecuación de reacción

sulfur dioxide

n-Butyllithium

sodium acetate trihydrate

hydroxylamine-O-sulfonic acid

product

2H-Thieno[3,2-e]-1,2,3-thiadiazine-1,1-dioxide

→

2H-Thieno[3,2-e]-1,2,3-thiadiazine-6-sulfonamide 1,1-dioxide

Disolventes

water

—

hexanes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to room temperature
2. 2
   OtroEvaporation of the reaction mixture
3. 3
   Otroprovided a residue which
4. 4
   Temperaturathis solution was cooled to 0° C.
5. 5
   ExtracciónThe reaction mixture was extracted with ethyl acetate (2×5 mL)
6. 6
   SecadoThe combined extracts were dried over MgSO4
7. 7
   Concentraciónconcentrated to a crude oil which
8. 8
   Otrowas purified by flash column chromatography (silica, hexane-ethyl acetate gradient)
9. 9
   Otroto give a white solid
10. 10
    Otrot>183° C

Procedimiento

The product from step B (0.1 g, 5.3 mmol) was dissolved in dry THF (4 mL) and cooled to -78° C. under nitrogen. n-Butyllithium (0.7 mL of a 2.5 M solution in hexanes, 1.75 mmol) was added dropwise, the mixture 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 reaction mixture provided a residue which was dissolved in water (5 mL) to which was added sodium acetate trihydrate (0.21 g, 1.39 mmol); this solution was cooled to 0° C. and hydroxylamine-O-sulfonic acid (0.18 g, 1.39 mmol) was added followed by stirring for 18 h. The reaction mixture was extracted with ethyl acetate (2×5 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 give a white solid. (0.021 g, 15%). decomposition:t>183° C. Cl-MS m/e 268 (m+H)+. 1HNMR (DMSO-d6): δ:7.90 (1H, 1s, CH); 8.22 (2H, S, NH2 exchangeable); 8.34 (1H, 1s, CH=N).

Fuente