反应 #215757

反应方程式

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

溶剂

water

—

hexanes

THF

反应条件

后处理

1. 1
   温度to warm to room temperature
2. 2
   其他Evaporation of the volatiles
3. 3
   其他provided a residue which
4. 4
   温度This solution was cooled to 0° C.
5. 5
   萃取The reaction mixture was extracted with ethyl acetate (2×50 mL)
6. 6
   干燥The combined extracts were dried over MgSO4
7. 7
   浓缩concentrated to a crude oil which
8. 8
   其他was purified by flash column chromatography (silica, hexane-ethyl acetate gradient)
9. 9
   其他>163° C

实验过程

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).

来源