Hydrochloric Acid → (7,8-Difluoro-3-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)-oxoacetaldehyde oxime

HRID 729423

Reaktionsgleichung

Reaktionsgleichung von HRID 729423
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.[OH2:8].O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[F:25][C:26]1[CH:36]=[CH:35][C:29]2[NH:30][CH:31]([CH3:34])[CH2:32][O:33][C:28]=2[C:27]=1[F:37].Cl.Cl.[NH2:40]O>O.C(O)C>[F:25][C:26]1[CH:36]=[CH:35][C:29]2[N:30]([C:3](=[O:5])[CH:2]=[N:40][OH:8])[CH:31]([CH3:34])[CH2:32][O:33][C:28]=2[C:27]=1[F:37]

Komponenten

8

Edukt 5

HCID 313Hydrochloric Acid2×HCID 2707Chloral HydrateHCID 62649Sodium sulfate decahydrateHCID 443297Hydroxyamine hydrochlorideHCID 102197187,8-Difluoro-2,3-dihydro-3-methyl-4H-(1,4)benzoxazine

Produkt 1

HCID 73857481(7,8-Difluoro-3-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)-oxoacetaldehyde oxime

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
77.5 °C

Versuchsvorschrift

A solution of 8.27 g (50 mmol) of chloral hydrate in 125 mL of water is treated with 112.8 g (0.35 mmol) of sodium sulfate decahydrate. The mixture is stirred and treated with a solution of 7,8-difluoro-3-methyl-3,4-dihydro-2H-benz[1,4]oxazine (Chem. Pharm. Bull., 1984; 32:4907) hydrochloride prepared by dissolving 8.26 g (44.6 mmol) of the free base in 50 mmol of concentrated hydrochloric acid in 70 mL of 50% aqueous ethanol). The reaction is stirred and a solution of 9.8 g (140 mmol) of hydroxylamine hydrochloride in 50 mL of water is added. After heating at 75 to 80° C. for 3 hours, the reaction is stirred at room temperature overnight. The resulting precipitate is removed by filtration, washed with water, and the wet filter cake is dissolved in dichloromethane. The organic solution is washed with water, dried (MgSO4), decolorized with charcoal, filtered and concentrated in vacuo to give 10.5 g of the title compound, mp 188-190° C.

Aufarbeitung

  1. customprepared
  2. stirringThe reaction is stirred
  3. stirringthe reaction is stirred at room temperature overnight
  4. customThe resulting precipitate is removed by filtration
  5. washwashed with water
  6. dissolutionthe wet filter cake is dissolved in dichloromethane
  7. washThe organic solution is washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bd84b90d5ca542f285a9517cfa559188
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582627B2

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