2-Aminophenol → 2-(4-chlorophenyl)-3-oxo 3,4-dihyro-2H-1,4-benzoxazine

HRID 1198456

Reaktionsgleichung

Reaktionsgleichung von HRID 1198456
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])O.[Na+].Br[CH:15]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:16](Cl)=[O:17]>C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([CH:15]2[C:16](=[O:17])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[O:8]2)=[CH:20][CH:21]=1

Komponenten

7

Edukt 3

HCID 58012-AminophenolHCID 516892Sodium BicarbonateHCID 12575778Bromo-4-chlorophenylacetyl chloride

Produkt 1

HCID 108488972-(4-chlorophenyl)-3-oxo 3,4-dihyro-2H-1,4-benzoxazineAusbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-aminophenol (13.5 g) in ethyl acetate (150 ml) is added a solution of sodium hydrogen carbonate (15 g) in water (300 ml), and to the mixture is added dropwise a solution of α -bromo-4-chlorophenylacetyl chloride (32.2 g) in toluene with vigorous stirring under ice cooling. After the mixture is stirred at room temperature for one hour, the solvent in the organic layer is distilled off and the residue is dissolved in acetone. To the solution is added potassium carbonate (20 g), and the mixture is stirred at room temperature overnight. The solvent is distilled off and to the residue is added water. The mixture is extracted with ethyl acetate. The ethyl acetate layer is washed, dried and distilled to remove the solvent, and the residue is recrystallized from ethyl acetate-n-hexane to give 2-(4-chlorophenyl)-3-oxo 3,4-dihyro-2H-1,4-benzoxazine (24.0 g) as crystals. M.p. 180.5°-181.5° C.

Aufarbeitung

  1. stirringAfter the mixture is stirred at room temperature for one hour
  2. distillationthe solvent in the organic layer is distilled off
  3. dissolutionthe residue is dissolved in acetone
  4. additionTo the solution is added potassium carbonate (20 g)
  5. stirringthe mixture is stirred at room temperature overnight
  6. distillationThe solvent is distilled off and to the residue
  7. additionis added water
  8. extractionThe mixture is extracted with ethyl acetate
  9. washThe ethyl acetate layer is washed
  10. customdried
  11. distillationdistilled
  12. customto remove the solvent
  13. customthe residue is recrystallized from ethyl acetate-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-267574ecad19420bb0f49d0aefa2077c
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281592

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