Water → HCID 10490994, Verbindung

HRID 2111453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2111453
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[F:6][C:7]1[C:12]([CH:13]=[O:14])=[C:11]([F:15])[C:10]([F:16])=[C:9](F)[C:8]=1[F:18].C(Cl)(=O)C.O>CC(N(C)C)=O>[F:6][C:7]1[C:8]([F:18])=[C:9]([S:3][C:1](=[O:4])[CH3:2])[C:10]([F:16])=[C:11]([F:15])[C:12]=1[CH:13]=[O:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 69558PentafluorobenzaldehydeHCID 23670855Potassium ethanethioate

Produkt 1

HCID 10490994HCID 10490994, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Potassium thioacetate (1.28 g, 11.2 mmol) was added to a solution of pentafluorobenzaldehyde (1.24 mL, 10.2 mmol) in anhydrous DMA (20 mL). After a strong exotherm subsided, the mixture was stirred at rt for 30 min. Acetyl chloride (1.60 mL, 22.4 mmol) was added and the mixture was stirred for another 30 min, then poured into water and extracted twice with ethyl ether. The combined organic extracts were dried (Na2SO4) and evaporated to obtain an orange oil which was chromatographed (silica, CH2Cl2/hexanes, 2:3) affording a pale-yellow solid. Recrystallization from heptane gave white crystals (1.77 g, 69%). mp 86-87° C.; 1H NMR δ 2.53 (s, 3H), 10.30 (s, 1H); 13C NMR δ 30.9, 115.5, 117.2, 145.3, 148.7, 182.9, 187.9; FAB-MS obsd 252.9936, calcd exact mass 252.9946; Anal. Calcd. for C9H4F4O2S: C, 42.86; H, 1.60; S, 12.72. Found: C, 43.00; H, 1.71; S, 12.67.

Aufarbeitung

  1. stirringthe mixture was stirred for another 30 min
  2. extractionextracted twice with ethyl ether
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. customevaporated
  5. customto obtain an orange oil which
  6. customwas chromatographed (silica, CH2Cl2/hexanes, 2:3)
  7. customaffording a pale-yellow solid
  8. customRecrystallization from heptane

Quellen und Nachweise

ORD-Eintrag
ord-a8bda83b898c40b08e8f4ee7a8af8b39
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07518905B2

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