Salicylamide → 2,2-dibutyl-4-oxo-2,3-dihydro-4H-1,3-benzoxazine

HRID 1756886

Reaktionsgleichung

Reaktionsgleichung von HRID 1756886
[CH2:1]([C:5]([CH2:7][CH2:8][CH2:9][CH3:10])=[O:6])[CH2:2][CH2:3][CH3:4].[C:11]([NH2:20])(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:5]1([CH2:7][CH2:8][CH2:9][CH3:10])[NH:20][C:11](=[O:19])[C:12]2[CH:13]=[CH:15][CH:16]=[CH:17][C:18]=2[O:6]1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 5147SalicylamideHCID 104055-NonanoneHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 100840172,2-dibutyl-4-oxo-2,3-dihydro-4H-1,3-benzoxazineAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 20 g of dibutylketone, 19.3 g of salicylamide and 2.7 g of p-toluenesulfonic acid monohydrate is added to 300 ml of toluene and the mixture is refluxed overnight by making use of a dehydrator of Dean Stark. After cooling, the reaction mixture is washed, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate =95:5) to obtain 34 g of 2,2-dibutyl-4-oxo-2,3-dihydro-4H-1,3-benzoxazine as a yellow oil.

Aufarbeitung

  1. temperaturethe mixture is refluxed overnight
  2. temperatureAfter cooling
  3. washthe reaction mixture is washed
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate =95:5)

Quellen und Nachweise

ORD-Eintrag
ord-9efcac42f446489ba5cf5243c6c30bd3
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05442055

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