Water → HCID 21706573, compound

A suspension of potassium peroxymonosulfate (32.0 g) and water (120 mL) was added to a 2° C. solution of 3-(4-chlorobutyl)-2,5,5-trimethyl-4-thiazolidinone (8.0 g) and ethanol (80 mL) over a period of 30 minutes. The cold bath was removed an the resulting mixture was stirred at room temperature for 22 hours, after which ethyl acetate (200 mL) was added. The mixture was filtered, the insolubles washed with ethyl acetate (3×30 mL), and the combined filtrates were diluted with water (200 mL). The organic layer was separated, and the aqueous layer extacted with ethyl acetate (2×100 mL). The combined organic extracts were washed with saturated aqueous NaHCO3 (200 mL), water (200 mL), and brine (200 mL), dried (Na2SO4), and concentrated in vacuo to 8.62 g of an off-white solid. The sulfone was recrystallized from ether to give 5.67 g (62.4%) of a white crystalline solid, m.p. 71°-73° C.

1. customThe cold bath was removed an the resulting mixture
2. additionafter which ethyl acetate (200 mL) was added
3. filtrationThe mixture was filtered
4. washthe insolubles washed with ethyl acetate (3×30 mL)
5. additionthe combined filtrates were diluted with water (200 mL)
6. customThe organic layer was separated
7. washThe combined organic extracts were washed with saturated aqueous NaHCO3 (200 mL), water (200 mL), and brine (200 mL)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated in vacuo to 8.62 g of an off-white solid
10. customThe sulfone was recrystallized from ether

ORD record

ord-d4df24a1b8774149bca3f0c9f7b44332

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05371087