Thiirane → HCID 23035055, compound

A solution of silver nitrate (1.31 g, 7.68 mmol) in water (4 ml) was added to a stirred solution of sodium 4-pyridylmethylsulfonate (1.50 g, 7.68 mmol) in water (15 ml). The resulting hazy solution was treated with ethylene sulfide (0.51 ml, 8.58 mmol) added dropwise over 2 minutes. The resulting gummy mixture was let stand at room temperature 30 minutes and the supernatant decanted. The residue was mixed with water (10 ml) and vigorously bubbled with hydrogen sulfide for 10 minutes. The mixture was vigorously stirred an additional 1 hour and the silver sulfide precipitate removed by centrifugation. The supernatant was concentrated under vacuum to ca. 5 ml and charged onto a column of Dowex 50W-X4 (hydrogen form, 200-400 mesh, 1.5×33 cm). The column was eluted with water at 6.0 ml fractions/2.0 minutes. Fractions 19 to 27 were combined and evaporated under vacuum to an off-white solid. The solid was mixed with a few mls of methanol and filtered to afford the title compound as an off-white solid (303 mg).

1. additionadded dropwise over 2 minutes
2. customat room temperature
3. custom30 minutes
4. customvigorously bubbled with hydrogen sulfide for 10 minutes
5. customthe silver sulfide precipitate removed by centrifugation
6. concentrationThe supernatant was concentrated under vacuum to ca. 5 ml
7. additioncharged onto a column of Dowex 50W-X4 (hydrogen form, 200-400 mesh, 1.5×33 cm)
8. washThe column was eluted with water at 6.0 ml fractions/2.0 minutes
9. customevaporated under vacuum to an off-white solid
10. additionThe solid was mixed with a few mls of methanol
11. filtrationfiltered

ORD record

ord-768bcdf8ab4f441a857567e5540f5db5

Source dataset

uspto-grants-1990_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04952397