Potassium Carbonate → HCID 63803879, Verbindung

HRID 2054157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2054157
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([SH:9])=[N:7][CH:8]=1.F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([S:9][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)=[N:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 178506226HCID 178506226, Verbindung

Produkt 1

HCID 63803879HCID 63803879, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 5-trifluoromethyl-pyridine-2-thiol (6.99 g, 39.0 mmol), 4-fluorobenzaldehyde (4.79 g, 38.6 mmol), anhydrous K2CO3 (8.16 g, 59.1 mmol) and DMF (70 mL) was heated at 110° C. for 18 h. The mixture was cooled to room temperature and partitioned between MTBE and water. The phases were separated. The organic extracts were combined, dried over Na2SO4, filtered and evaporated to give a crude product which was purified by flash column chromatography (eluent: 5% MTBE in petroleum ether). Evaporation of the appropriate fractions gave the product (9.47 g, 87% yield). 1H NMR (CDCl3) δ 10.06 (s, 1H), 8.69-8.66 (m, 1H), 7.97-7.92 (m, 2H), 7.78-7.72 (m, 3H), 7.23-7.16 (m, 1H).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between MTBE and water
  3. customThe phases were separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude product which
  8. customwas purified by flash column chromatography (eluent: 5% MTBE in petroleum ether)
  9. customEvaporation of the appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-aade7da85b054679afdbb4e4882f4c5f
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07329656B2

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