Methyl iodide → 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-methylsulfanyl-2-propenenitrile

HRID 279101

Reaktionsgleichung

Reaktionsgleichung von HRID 279101
[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:14](=O)([O-])[O-].[K+].[K+].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([N:30]=[C:31]=[S:32])[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1.CI>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11](=[C:31]([NH:30][C:24]2[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=[C:22]([O:21][CH3:20])[CH:23]=2)[S:32][CH3:14])[C:12]#[N:13])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1454223,5-Dimethoxyphenyl isothiocyanateHCID 7358292-(4-Chlorobenzenesulfonyl)acetonitrile

Produkt 1

HCID 701503682-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-methylsulfanyl-2-propenenitrileAusbeute 65 %

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 3,5-dimethoxyphenyl isothiocyanate (0.96 g, 4.9 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 2 h 15 min and then filtered. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 4 h. The reaction mixture was concentrated. The residue was dissolved in DCM, washed with water, dried (Na2SO4) and concentrated. The residue was crystallised from ethyl acetate/heptane 1:2 to give 1.27 g (65%) of the title compound. Mp 119.5-123° C.; 1H NMR (200 MHz, CDCl3): δ=2.29 (s, 3H), 3.80 (s, 6H), 3.36 (m, 3H), 7.53 (d, 2H), 7.87 (d, 2H), 9.82 (br s, 1H); EI SP/MS: 424 (M+).

Aufarbeitung

  1. filtrationfiltered
  2. stirringThe mixture was stirred at room temperature for 4 h
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionThe residue was dissolved in DCM
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was crystallised from ethyl acetate/heptane 1:2

Quellen und Nachweise

ORD-Eintrag
ord-5a4ef250dd0c4321a80a5e13b012f5b9
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362205B1

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