4-(Methylsulfanyl)thiophenol → HCID 22663926, Verbindung

HRID 392284

Reaktionsgleichung

Reaktionsgleichung von HRID 392284
Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1>CN(C=O)C>[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:2]2[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 1368964-(Methylsulfanyl)thiophenolHCID 140466744-Chloropyridine-3-carbaldehyde

Produkt 1

HCID 22663926HCID 22663926, VerbindungAusbeute 114,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4-Chloronicotinaldehyde [prepared according to D. Albanese, M. Penso, M. Zenoni, Synthesis 1999, 1294-1296] (500 mg, 3.5 mmol), 4-methylsulfanyl-benzenethiol (606 mg, 3.88 mmol) potassium carbonate (586 mg, 4.24 mmol) and DMF (7 mL) were combined, the mixture was heated together at 50° C. for 1.5 h and then stirred at room temperature overnight. The solvent was removed in vacuo and the residue was partitioned between EtOAc (100 mL) and 10% aqueous K2CO3 (100 mL). The organic layer was dried (MgSO4) and evaporated to give the title compound (1.05 g) as a yellow oil. The 1H NMR spectrum showed the material to be of sufficient purity (90-95%) to be used without further purification; δH (CDCl3, 400 MHz) 2.54 (3H, s), 6.69 (1H, d), 7.35 (2H, d), 7.4 (2H, d), 8.35 (1H, d), 8.87 (1H, s), 10.24 (1H, s); MS m/z (TS+) 262 (MH+).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc (100 mL) and 10% aqueous K2CO3 (100 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8ac8bc349ff6476ab5621429455c11f1
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800652B2

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