Methyl iodide → 3-(Benzo[1,3]dioxol-5-ylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile

HRID 279134

Reaktionsgleichung

Reaktionsgleichung von HRID 279134
[CH3:1][S:2]([CH2:5][C:6]#[N:7])(=[O:4])=[O:3].[C:8](=O)([O-])[O-].[K+].[K+].[CH2:14]1[O:22][C:21]2[CH:20]=[CH:19][C:18]([N:23]=[C:24]=[S:25])=[CH:17][C:16]=2[O:15]1.CI>CC(C)=O>[O:22]1[C:21]2[CH:20]=[CH:19][C:18]([NH:23][C:24]([S:25][CH3:8])=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]#[N:7])=[CH:17][C:16]=2[O:15][CH2:14]1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 75283(Methylsulfonyl)acetonitrileHCID 1235931,3-Benzodioxole, 5-isothiocyanato-

Produkt 1

HCID 701495853-(Benzo[1,3]dioxol-5-ylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrileAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of methanesulfonylacetonitrile (2.85 g, 23.9 mmol) in dry acetone (50 ml) was stirred while dry potassium carbonate (6.61 g, 47.8 mmol) and 3,4-methylenedioxyphenyl isothiocyanate (4.50 g, 25.1 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 20 h. Excess of potassium carbonate was filtered off, methyl iodide (4.43 ml, 71.8 mmol) was added to the filtrate, and stirring was continued for 4 h at 50° C. The mixture was evaporated and the residue was dissolved in dichloromethane and extracted with water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to afford 4.88 g (65%) of the title compound as golden brown crystals. Mp 168-170° C.1H NMR (200 MHz, DMSO-d6): δ=2.30 (s, 3H), 3.33 (s, 3H), 6.06 (s, 2H), 6.79 (dd, 1H), 6.94 (d, 1H), 6.97 (d, 1H), 9.98 (br s, 1H).

Aufarbeitung

  1. additionwere added
  2. filtrationExcess of potassium carbonate was filtered off
  3. stirringstirring
  4. waitwas continued for 4 h at 50° C
  5. customThe mixture was evaporated
  6. dissolutionthe residue was dissolved in dichloromethane
  7. extractionextracted with water and brine
  8. dry with materialThe organic phase was dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-27b4340d3d1442bdbf7c7fd30c7156c8
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362205B1

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