Dimethyl Sulfoxide → 2-Benzoxazol-2-yl-3,3-bismethylsulfanylacrylonitrile

HRID 2261635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261635
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]#[N:12].[C:13](=S)=[S:14].IC.[H-].[Na+].[CH3:20][S:21]([CH3:23])=O>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=[C:20]([S:14][CH3:13])[S:21][CH3:23])[C:11]#[N:12]

Komponenten

6

Edukt 5

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 8433252-(1,3-Benzoxazol-2-yl)acetonitrile

Produkt 1

HCID 129138932-Benzoxazol-2-yl-3,3-bismethylsulfanylacrylonitrileAusbeute 57 %

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a solution of benzoxazol-2-ylacetonitrile (2.07 g, 13.1 mmol) dissolved in 35 mL of DMSO at room temperature under argon atmosphere was added carbon disulfide (1.10 g, 14.4 mmol) followed by iodomethane (5.20 g, 36.7 mmol). This solution was then cooled to 10° C. and sodium hydride (1.05 g, 60% by wt in oil, 26.3 mmol) was added over a period of several minutes. The solution was allowed to warm to room temperature and stirred overnight. The reaction was then quenched with an ammonium chloride solution and was extracted with 5×50 mL of ethyl acetate. The ethyl acetate was washed with brine solution (3×50 mL) and water (3×30 mL). The organic phase was dried over magnesium sulfate, filtered, and evaporated to yield a red oil. The crude material was purified by flash column chromatography eluting with CH2Cl2:MeOH=98:2 to yield 1.96 g (57%) of the desired product as a yellow oil. MS (m/z, ES+): 236.68 (M+1, 100%).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customThe reaction was then quenched with an ammonium chloride solution
  3. extractionwas extracted with 5×50 mL of ethyl acetate
  4. washThe ethyl acetate was washed with brine solution (3×50 mL) and water (3×30 mL)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a red oil
  9. customThe crude material was purified by flash column chromatography
  10. washeluting with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-4a287f29b8b44b17abde4fe2edaf818b
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07847101B2

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