hydroxylamine-O-sulfonic acid → 4-Chlorothieno[3,2-c]pyridine-2-sulfonamide

To a solution of 4-chlorothieno[3,2-c]pyridine (1.7 g, 10 mmol) in distilled tetrahydrofuran (25 ml), cooled to -70° C. and under a nitrogen atmosphere, was added dropwise 0.7 M lithium diisopropylamide in THF (16 ml, 11 mmol) to give a clear solution. After 178 hour, sulfur dioxide gas was bubbled over the reaction surface and it was gradually let warm to room temperature. The mixture was diluted with diethyl ether and the precipitated lithium sulfinate salt was collected by filtration. This salt (3.1 g) 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 18 hours, the precipitated product was collected by filtration, dissolved in ethyl acetate, dried over anhydrous sodium sulfate, filtered through a pad of charcoal and the solvent was evaporated. The residue was recrystallized from ethyl acetate to give 1.23 g (49% yield) purified product.

1. customto give a clear solution
2. customsulfur dioxide gas was bubbled over the reaction surface and it
3. additionThe mixture was diluted with diethyl ether
4. filtrationthe precipitated lithium sulfinate salt was collected by filtration
5. dissolutionThis salt (3.1 g) was dissolved in water (25 ml)
6. filtrationthe precipitated product was collected by filtration
7. dissolutiondissolved in ethyl acetate
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered through a pad of charcoal
10. customthe solvent was evaporated
11. customThe residue was recrystallized from ethyl acetate
12. customto give 1.23 g (49% yield)
13. custompurified product

ORDレコード

ord-acbd16478e7e48d1a213c0a4f5114cc9

出典データセット

uspto-grants-1988_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04731368