Potassium Hydroxide → 2-Amino-6-m-fluorophenyl-1,3-oxazine-4-one

HRID 483226

Reaktionsgleichung

Reaktionsgleichung von HRID 483226
S(O)(O)(=O)=O.C[NH:7][C:8](=[NH:10])S.[OH-].[K+].C([O:15][C:16](=O)[CH2:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)C.O1C=CC=CN1>O>[NH2:10][C:8]1[O:26][C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[CH:17][C:16](=[O:15])[N:7]=1

Komponenten

6

Edukt 4

HCID 14797Potassium HydroxideHCID 2063904Ethyl 3-(3-fluorophenyl)-3-oxopropanoateHCID 12313776OxazineHCID 178485225HCID 178485225, Verbindung

Produkt 1

HCID 133709352-Amino-6-m-fluorophenyl-1,3-oxazine-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To 16.6 g (0.597M) of methylthiopseudourea sulfate is added 66 ml of H2O+13.0 g of KOH. With vigorous stirring, 20 g (71.9 mM) of ethyl-m-fluorobenzoylacetate is added and the reaction mixture is allowed to stir, at ambient temperature, for 18 hours. The solids are filtered and washed well with H2O followed by diethylether. The crude title compound is dried at 60° C. in a vacuum over to yield 16.0 g (>100 percent). To 6.8 g of crude powdered oxazine is added 100 ml of H2O and heated to 70° C., cooled, filtered and washed solids. Yield of 2-amino-6-m-fluorophenyl-1,3-oxazine-4-one of 3.60 g (53 percent of rec. yield).

Aufarbeitung

  1. filtrationThe solids are filtered
  2. washwashed well with H2O
  3. dry with materialThe crude title compound is dried at 60° C. in a vacuum over
  4. customto yield 16.0 g (>100 percent)
  5. temperatureheated to 70° C.
  6. temperaturecooled
  7. filtrationfiltered
  8. washwashed solids

Quellen und Nachweise

ORD-Eintrag
ord-753e89259edd461a8405e9c4f059df07
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04578466

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