Heptane → 4-(1,3-Oxazol-5-yl)benzonitrile

HRID 659738

Reaktionsgleichung

Reaktionsgleichung von HRID 659738
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[O:2].S([CH2:21][N+:22]#[C-:23])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].CCCCCCC>CO>[O:2]1[C:1]([C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)=[CH:23][N:22]=[CH:21]1

Komponenten

6

Edukt 4

HCID 8900HeptaneHCID 11430Potassium CarbonateHCID 660424-CyanobenzaldehydeHCID 161915Tosylmethyl isocyanide

Produkt 1

HCID 27772714-(1,3-Oxazol-5-yl)benzonitrileAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-Formyl-benzonitrile (5 g, 38.17 mmol) and tosylmethyl isocyanide (TosMIC) (from Aldrich, 8.33 g, 42 mmol) in MeOH (200 mL) was added K2CO3 (6.85 g, 49.62 mmol) and the mixture was stirred at reflux for 1 h. The solvent was then evaporated and saturated aqueous NaHCO3 was added. The resultant suspension was extracted with dichloromethane (3×100 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous MgSO4 and concentrated to leave a yellow solid. Trituration with heptane afforded a solid that was collected by filtration and dried under vacuum to give the title compound (6.3 g, 97%). m.p.=140° C.

Aufarbeitung

  1. temperatureat reflux for 1 h
  2. customThe solvent was then evaporated
  3. additionsaturated aqueous NaHCO3 was added
  4. extractionThe resultant suspension was extracted with dichloromethane (3×100 mL)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customto leave a yellow solid
  9. filtrationthat was collected by filtration
  10. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ee884524aae24f788390cbf66120db83
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080669B2

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