Potassium Chloride → 3,4-dihydro-2H-1,4-benzoxazine-2-carbonitrile

HRID 1483029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1483029
Cl[C:2](=[CH2:5])[C:3]#[N:4].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].[Cl-].[K+]>CC(C)=O>[O:13]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][CH2:5][CH:2]1[C:3]#[N:4]

Komponenten

5

Edukt 3

HCID 4873Potassium ChlorideHCID 58012-AminophenolHCID 701982-Chloroacrylonitrile

Produkt 1

HCID 27955043,4-dihydro-2H-1,4-benzoxazine-2-carbonitrileAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Combine 2-chloro-2-propenenitrile (3.0 g, 34.3 mmol), 2-aminophenol (3.27 g, 29.96 mmol), acetone (50 mL), and potassium chloride (5 g, 36.18 mmol). Stir the mixture at ambient temperature for 16 hours. Filter the mixture and wash the filter cake with EtOAc. Concentrate the filtrate under reduced pressure to give a residue. Purify via flash column chromatography using a gradient of 1-50% EtOAc in petroleum ether to elute. Combine the product fractions and remove solvents under reduced pressure to provide the title compound (1.5 g, 21.6%). MS (m/z): 161 (M+1).

Aufarbeitung

  1. filtrationFilter the mixture
  2. washwash the filter cake with EtOAc
  3. concentrationConcentrate the filtrate under reduced pressure
  4. customto give a residue
  5. customPurify via flash column chromatography
  6. washto elute
  7. customCombine the product fractions and remove solvents under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bd0f5f84560741e393df1207e8f4711f
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09416138B2

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