تفاعل #656240

معادلة التفاعل

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

المردود 59.0%

المذيبات

tetrahydrofuran

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر