Water → 5-Acetyl-4-methylthiazole

HRID 1906021

Reaktionsgleichung

Reaktionsgleichung von HRID 1906021
[C:1]([C:4]1[S:8][C:7](N)=[N:6][C:5]=1[CH3:10])(=[O:3])[CH3:2].C(ON=O)CC(C)C.C(OCC)(=O)C.O>O1CCCC1.CN(C)C=O>[C:1]([C:4]1[S:8][CH:7]=[N:6][C:5]=1[CH3:10])(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8053Isoamyl NitriteHCID 8857Ethyl AcetateHCID 7208825-Acetyl-2-amino-4-methylthiazole

Produkt 1

HCID 1622925-Acetyl-4-methylthiazoleAusbeute 54,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-acetyl-2-amino-4-methylthiazole (15.6 g) in a mixture of tetrahydrofuran (200 ml) and dimethylformamide (50 ml) was dropwise added isoamylnitrite (14.6 g) at 50° C. to 55° C. with stirring and the mixture was stirred at 55° C. to 60° C. for 4 hours. The reaction mixture was poured into a mixture of ethyl acetate and water with stirring. The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was subjected to column chromatography on silica gel and eluted with a mixture of diisopropyl ether and ethyl acetate (1:1). The fractions containing the desired compound were combined and evaporated in vacuo to give 5-acetyl-4-methylthiazole (7.7 g) as an oil.

Aufarbeitung

  1. customat 50° C. to 55° C.
  2. stirringthe mixture was stirred at 55° C. to 60° C. for 4 hours
  3. stirringwith stirring
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. washeluted with a mixture of diisopropyl ether and ethyl acetate (1:1)
  8. additionThe fractions containing the desired compound
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-872368eeea9a495388984f5a0e5a3908
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04649146

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