Methyl iodide → 3-(4-Chlorophenylamino)-2-methylsulfonyl-3-methylsulfanyl-propenenitrile

HRID 279121

Reaktionsgleichung

Reaktionsgleichung von HRID 279121
[CH3:1][S:2]([CH2:5][C:6]#[N:7])(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[S:23])=[CH:17][CH:16]=1.[CH3:24]I>CC(C)=O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([S:23][CH3:24])=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]#[N:7])=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 164804-Chlorophenyl isothiocyanateHCID 75283(Methylsulfonyl)acetonitrile

Produkt 1

HCID 701491873-(4-Chlorophenylamino)-2-methylsulfonyl-3-methylsulfanyl-propenenitrileAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of methanesulfonylacetonitrile (0.55 g, 4.9 mmol) in dry acetone (5 ml) first dry potassium carbonate (1.28 g, 9.3 mmol) and then 4-chlorophenyl isothiocyanate (0.78 g, 4.6 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 22 h, and then filtered. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 2 h. The precipitate was filtered off, the filtrate was concentrated. The residue was taken up into dichloromethane and water. The organic layer was washed with water (2×), dried (sodium sulfate) and concentrated. Crystallisation from ethyl acetate gave 1.114 g (80%) of the title compound. 1H NMR (200 MHz, CDCl3): δ=2.25 (s, 3H), 3.20 /s, 3H), 7.25 (d, 2H), 7.41 (d, 2H), 9.70 (br s, 1H); EI SP/MS: 302 (M+), 304 (M+2).

Aufarbeitung

  1. filtrationfiltered
  2. stirringThe mixture was stirred at room temperature for 2 h
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated
  5. washThe organic layer was washed with water (2×)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customCrystallisation from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-de3b83c3a84c43fdb7fa43ff3ffe98fc
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362205B1

Verknüpfte Notizen

Wird geladen…