Water → 6-amino-4-propargyl-2H-1,4-benzoxazin-3(4H)-one

HRID 235586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 235586
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[NH:9][C:8]=2[CH:14]=1.[CH2:15](Cl)[C:16]#[CH:17].O>CN(C)C=O>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[N:9]([CH2:17][C:16]#[CH:15])[C:8]=2[CH:14]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 122213-Chloro-1-propyneHCID 24758Sodium hydrideHCID 27636816-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one

Produkt 1

HCID 136490056-amino-4-propargyl-2H-1,4-benzoxazin-3(4H)-oneAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (0.08 g) was suspended in dry N,N-dimethylformamide (3 ml), and the suspension was cooled to 0° C. While stirring, 6-amino-2H-1,4-benzoxazin-3(4H)-one (0.5 g) was portionwise added to the suspension at 0° C., and the resultant mixture was stirred at the same tempeature for 30 minutes. To the mixture, propargyl chloride (0.25 g) was dropwise added, and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with water, dried and concentrated to give 6-amino-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (0.36 g). m.p., 260.1° C.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 6 hours
  2. extractionwas then extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ce73d69614134d8da3484c2afa87b6a0
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640707

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