Thiazolidinedione → 3-Ethyl-2,4-thiazolidinedione

Temperature

50 °C

To a 100 ml three necked round bottom flask, sodium hydride (60% in paraffin) (0.188 g, 0.00470 mole) was taken in DMF (2.0 ml). Thiazolidine-2,4-dione (0.5 g, 0.00427 mole) in DMF (3 ml) was slowly added at 0° C. over 15 min under nitrogen atmosphere. After addition was complete, the reaction mixture was stirred for 1 hr at 50° C. The reaction was then cooled to 0° C., followed by drop wise addition of ethyl iodide (0.41 ml, 0.00512 mole) at 0° C. The reaction mixture was warmed up to RT and stirred for 1 hr. After completion of the reaction, the reaction mixture was poured in water and aq. layer was extracted with ethyl acetate. Organic layers were combined and washed with brine solution, dried over Na2SO4, filtered and concentrated to afford crude product which was purified using column purification by eluting the compound with 5% ethyl acetate in hexanes to yield 0.5 g of 3-ethylthiazolidine-2,4-dione.

1. additionAfter addition
2. temperatureThe reaction was then cooled to 0° C.
3. temperatureThe reaction mixture was warmed up to RT
4. stirringstirred for 1 hr
5. customAfter completion of the reaction
6. extractionaq. layer was extracted with ethyl acetate
7. washwashed with brine solution
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto afford crude product which
12. customwas purified
13. customcolumn purification
14. washby eluting the compound with 5% ethyl acetate in hexanes

ORD record

ord-ea2852ca82b34478bb377f0959d75412

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187487B2