Allyl bromide → 2,2-Dimethyl-6-[(prop-2-en-1-yl)oxy]-2,3-dihydro-4H-1,3-benzoxazin-4-one

HRID 615236

Reaktionsgleichung

Reaktionsgleichung von HRID 615236
[CH3:1][C:2]1([CH3:14])[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:4]=2[O:3]1.[CH2:15](Br)[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1([CH3:14])[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([O:13][CH2:17][CH:16]=[CH2:15])[CH:11]=[CH:12][C:4]=2[O:3]1

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 137543316-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1,3-benzoxazin-4-one

Produkt 1

HCID 137544162,2-Dimethyl-6-[(prop-2-en-1-yl)oxy]-2,3-dihydro-4H-1,3-benzoxazin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 9.65 g of 2,3-dihydro-2,2-dimethyl-6-hydroxy-4H-1,3-benzoxazin-4-one and 9.1 g of allyl bromide in 150 ml of acetonitrile is refluxed for 5 hours, whilst stirring, with the addition of 10.3 g of dry potassium carbonate. The reaction mixture is filtered whilst warm, the filtrate is concentrated by evaporation and the remaining crystals are suction-filtered after trituration with ether. The crude 2,3-dihydro-2,2-dimethyl-6-(1-propen-3-yloxy)-4H-1,3-benzoxazin-4-one obtained in this manner melts at 137°-138°.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. temperaturewhilst warm
  3. concentrationthe filtrate is concentrated by evaporation
  4. filtrationthe remaining crystals are suction-filtered after trituration with ether

Quellen und Nachweise

ORD-Eintrag
ord-e6886a16c1dc499a952b51d1e4d15de8
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04497813

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