Potassium Carbonate → (4,4-Difluorobut-3-enylthio)-3-methyl-1,2,4-thiadiazole

To a solution of 3-methyl-1,2,4-thiadiazole-5(4H)-thione (1.2 g) in acetone (100 cm3) was added 4,4-difluorobut-3-enyl 4-methylbenzenesulfonate (2.4 g) and potassium carbonate (1.2 g) and the mixture was refluxed for 4 hours after which tlc indicated complete consumption of starting material. The reaction was poured into ethyl acetate and water and the layers separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried (MgSO4). The solution of product was then filtered and evaporated under reduced pressure to give a brown oil which was purified by flash chromatography (silica, 7% ethyl acetate in hexane) to give 5-(4,4-difluorobut-3-enylthio)-3-methyl-1,2,4-thiadiazole as a brown oil (0.645 g). M+ =222; 1H NMR: δ 2.56(2H, br q); 2.63 (3H,s); 3.30(2H,t); 4.30(1H,m).

1. temperaturethe mixture was refluxed for 4 hours after which tlc
2. customconsumption of starting material
3. additionThe reaction was poured into ethyl acetate and water
4. customthe layers separated
5. extractionThe aqueous layer was extracted with ethyl acetate
6. dry with materialthe combined organic layers were dried (MgSO4)
7. filtrationThe solution of product was then filtered
8. customevaporated under reduced pressure
9. customto give a brown oil which
10. customwas purified by flash chromatography (silica, 7% ethyl acetate in hexane)

ORD 기록

ord-fcd1944e9cd145cd909a02b72e8dbb72

출처 데이터셋

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05912243