HCID 13770581, Verbindung → 4-tert-Butyl-2-(3-methyl-2-oxopyrrolidin-1-yl)furan-3-carbonitrile

HRID 236224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236224
[NH2:1][C:2]1[O:3][CH:4]=[C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]=1[C:7]#[N:8].[CH3:13][CH:14]([CH2:18][CH2:19]Cl)[C:15](Cl)=[O:16]>C1(C)C=CC=CC=1>[C:7]([C:6]1[C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][O:3][C:2]=1[N:1]1[CH2:19][CH2:18][CH:14]([CH3:13])[C:15]1=[O:16])#[N:8]

Komponenten

4

Edukt 2

HCID 13770581HCID 13770581, VerbindungHCID 137705824-Chloro-2-methylbutanoyl chloride

Produkt 1

HCID 1748554-tert-Butyl-2-(3-methyl-2-oxopyrrolidin-1-yl)furan-3-carbonitrileAusbeute 21,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To 4.0 g of 2-amino-3-cyano-4-(1,1-dimethylethyl)furan and 4.3 g of 2-methyl-4-chlorobutyryl chloride was added 150 ml of toluene. The reaction mixture was allowed to reflux for about 72 hours. The mixture was washed once with 1N hydrochloric acid, once with 2N sodium hydroxide and finally with water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was chromatographed over silica gel while eluting with an 80/20 mixture of Skellysolve B/ethyl acetate. Fractions containing the major component were combined and the solvent was evaporated therefrom to afford 1.3 g of N-[3-cyano-4-(1,1-dimethylethyl)-2-furyl]-3-methyl-2-pyrrolidinone. mp=88°-90° C. Yield 21%.

Aufarbeitung

  1. temperatureto reflux for about 72 hours
  2. washThe mixture was washed once with 1N hydrochloric acid, once with 2N sodium hydroxide and finally with water
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was chromatographed over silica gel
  7. washwhile eluting with an 80/20 mixture of Skellysolve B/ethyl acetate
  8. additionFractions containing the major component
  9. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ee6519c414f943b6973ab1c04f62407c
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04643758

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