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

HRID 279093
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 279093
[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
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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-6d1fe10259b544d98becbfeb1471f09e
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06362205B1

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