Methyl iodide → Thiophene-3-carbonitrile, 5-acetyl-4-(4-chlorophenyl)-2-methylthio-

HRID 478177

Reaktionsgleichung

Reaktionsgleichung von HRID 478177
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]#[N:11])=[CH:4][CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].[C:19](=[S:21])=[S:20].Cl[CH2:23][C:24](=[O:26])[CH3:25].CI>CN(C=O)C>[C:24]([C:25]1[S:20][C:19]([S:21][CH3:13])=[C:9]([C:10]#[N:11])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:26])[CH3:23]

Komponenten

7

Edukt 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 1383084-Chlorobenzoylacetonitrile

Produkt 1

HCID 627943Thiophene-3-carbonitrile, 5-acetyl-4-(4-chlorophenyl)-2-methylthio-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

3-(4-chloro-phenyl)-3-oxo-propionitrile (5 mmol) was added to a suspension of K2CO3 (3 equivalents, 15 mmol) in DMF (4.5 mL) and allowed to stir at room temperature. After 10 minutes, CS2 (1.25 equivalents, 7.5 mmol) was added in one portion and the resulting mixture stirred at room temperature for an additional 10 minutes then a solution of 1-chloro-propan-2-one (1.0 equivalent, 5 mmol) in DMF (5 mL) was added. After 1 hour, a solution of MeI (1.1 equivalents, 5.5 mmol) in DMF (2 mL) was added in a dropwise fashion then, after 30 minutes, the mixture was poured onto water and the resulting mixture was stirred vigorously for 12-16 hours to afford a suspension of the desired product. The crude product was isolated by filtration.

Aufarbeitung

  1. stirringthe resulting mixture stirred at room temperature for an additional 10 minutes
  2. waitAfter 1 hour
  3. waitafter 30 minutes
  4. additionthe mixture was poured onto water
  5. stirringthe resulting mixture was stirred vigorously for 12-16 hours
  6. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-c1c567d9aefe4d589a3edf3b5dbf3d54
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642227B2

Verknüpfte Notizen

Wird geladen…