반응 #656240

반응 방정식

thieno[3,2-c]pyridin-4(5H)-one

lithium diisopropylamide

sodium acetate trihydrate

hydroxylamine-O-sulfonic acid

→

2-Sulfamoylthieno[3,2-c]pyridin-4(5H)-one

수율 59.0%

용매

tetrahydrofuran

THF

반응 조건

후처리

1. 1
   기타sulfur dioxide gas was bubbled over the surface of this suspension
2. 2
   온도to gradually warm to room temperature
3. 3
   workup.ADDITIONThe mixture was diluted with diethyl ether
4. 4
   기타the precipitated lithium sulfinate intermediate was collected (3.6 g)
5. 5
   workup.DISSOLUTIONThis salt was dissolved in water (25 ml)
6. 6
   여과the precipitated product was collected by filtration
7. 7
   기타The product was purified by recrystallization from hot dimethyl sulfoxide by dilution with ethanol
8. 8
   기타to give 1.35 g (59% yield)

실험 절차

To a suspension of thieno[3,2-c]pyridin-4(5H)-one (1.51 g, 10 mmol) in distilled tetrahydrofuran (20 ml), cooled to -70° C. and under a nitrogen atmosphere, was added dropwise 0.7 M lithium diisopropylamide in THF (36 ml, 25 mmol). After one hour, sulfur dioxide gas was bubbled over the surface of this suspension and the reaction was allowed to gradually warm to room temperature. The mixture was diluted with diethyl ether and the precipitated lithium sulfinate intermediate was collected (3.6 g). This salt was dissolved in water (25 ml) and sodium acetate trihydrate (5.4 g, 66 mmol) and hydroxylamine-O-sulfonic acid (2.5 g, 22 mmol) were added. After stirring for 16 hours, the precipitated product was collected by filtration. The product was purified by recrystallization from hot dimethyl sulfoxide by dilution with ethanol to give 1.35 g (59% yield); m.p. 300°-301° C.

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