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

HRID 725009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 725009
[CH3:1][C:2]1[NH:6][C:5](=[S:7])[S:4][N:3]=1.CC1C=CC(S(O[CH2:19][CH2:20][CH:21]=[C:22]([F:24])[F:23])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:23][C:22]([F:24])=[CH:21][CH2:20][CH2:19][S:7][C:5]1[S:4][N:3]=[C:2]([CH3:1])[N:6]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 11666101HCID 11666101, VerbindungHCID 1784347993-methyl-1,2,4-thiadiazole-5-thiol

Produkt 1

HCID 21850474(4,4-Difluorobut-3-enylthio)-3-methyl-1,2,4-thiadiazoleAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-cfc021c995cc4e58abbc88a90627f13a
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05705516

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