Potassium peroxymonosulphate → HCID 14390548, compound

To a stirred solution of 2-(2,2-dichloroethenyl)-5-(4-methylthiophenyl)thiophene (1.2 g, 0.0040 mole) in methanol (50 mL) was added a solution of potassium peroxymonosulfate (1.2 g, 0.0020 mole) in water (50 mL). After stirring for one hour at room temperature, an additional 0.3 g of potassium peroxymonosulfate was added, and a second addition of 0.3 g was made after an additional hour. After a total of about four hours of stirring at room temperature the mixture was extracted, first with diethyl ether, followed by methylene chloride. The extracts were combined and dried over anhydrous magnesium sulfate. The dried extract was filtered, and the filtrate was evaporated under reduced pressure leaving a solid residue. This residue was dissolved in isopropyl alcohol (15 mL), and a solution of potassium peroxymonosulfate (0.5 g) dissolved in about 5 mL of water was added. The resultant mixture was heated on a steam bath for approximately one hour. The mixture was diluted with 400 mL of water and cooled to 0° C. for one hour. A solid formed and was collected by filtration. The filter cake was dissolved in methylene chloride, and the solution was dried over anhydrous magnesium sulfate. The dried solution was filtered, and the filtrate was evaporated under reduced pressure, leaving a solid residue. This residue was purified by column chromatography on silica gel, eluting first with petroleum ether, followed by ethyl acetate, to yield 0.8 g of 2-(2,2-dichloroethenyl)-5-(4-methylsulfinylphenyl)thiophene as a solid (mp 124°-126° C.) .

1. additiona second addition of 0.3 g
2. waitwas made after an additional hour
3. stirringAfter a total of about four hours of stirring at room temperature the mixture
4. extractionwas extracted, first with diethyl ether
5. dry with materialdried over anhydrous magnesium sulfate
6. extractionThe dried extract
7. filtrationwas filtered
8. customthe filtrate was evaporated under reduced pressure
9. customleaving a solid residue
10. additionwas added
11. temperaturecooled to 0° C. for one hour
12. customA solid formed
13. filtrationwas collected by filtration
14. dissolutionThe filter cake was dissolved in methylene chloride
15. dry with materialthe solution was dried over anhydrous magnesium sulfate
16. filtrationThe dried solution was filtered
17. customthe filtrate was evaporated under reduced pressure
18. customleaving a solid residue
19. customThis residue was purified by column chromatography on silica gel
20. washeluting first with petroleum ether

ORD record

ord-498d94ae359a4600ac0c08c02fbd8ac4

Source dataset

uspto-grants-1988_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04782079