Methyl iodide → 2-(4-Chlorophenylsulfonyl)-3-methylsulfanyl-3-(pyridin-3-ylamino)-2-propenenitrile

HRID 840204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 840204
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]=[C:27]=[S:28])[CH:21]=1.[CH3:29]I>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11](=[C:27]([S:28][CH3:29])[NH:26][C:22]2[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=2)[C:12]#[N:13])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 7358292-(4-Chlorobenzenesulfonyl)acetonitrileHCID 27372423-Pyridyl isothiocyanate

Produkt 1

HCID 701501772-(4-Chlorophenylsulfonyl)-3-methylsulfanyl-3-(pyridin-3-ylamino)-2-propenenitrileAusbeute 17,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 4-chlorophenylsulfonylacetonitrile (1.00 g, 4.6 mmol) in dry acetone (10 ml) first dry potassium carbonate (1.28 g, 9.3 mmol) and then pyridin-3-yl isothiocyanate (0.663 g, 4.9 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 4 h, and then filtered. To the filtrate methyl iodide (0.315 ml, 5.1 mmol) was added. The mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated and the residue was taken up into ethyl acetate and water. The organic layer was washed with 1N aqueous HCl (2×). The organic phase was dried (sodium sulfate) and concentrated. The residue was purified by flash chromatography using heptane/ethyl acetate 1:2 as eluent and recrystallisation in ethyl acetate to give 294 mg (16%) of the title compound. Mp 181-182° C. 1H NMR (300 MHz, CDCl3): δ=2.20 (s, 3H), 7.36 (dd, 1H), 7.54 (dm, 2H), 7.6 (m, 1H), 7.88 (dm, 2H), 8.55 (m, 2H), 9.85 (br s, 1H); EI SP/MS: 365 (M+).

Aufarbeitung

  1. filtrationfiltered
  2. stirringThe mixture was stirred at room temperature for 16 h
  3. concentrationThe reaction mixture was concentrated
  4. washThe organic layer was washed with 1N aqueous HCl (2×)
  5. dry with materialThe organic phase was dried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. customrecrystallisation in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9d1ae3d99f7443e3b0960edb538cd349
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06365609B1

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