Boron tribromide → 3-(2-Fluoro-4-hydroxyphenyl)-1-isopropyl-2,4-imidazolidinedione

HRID 257363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 257363
B(Br)(Br)Br.[CH3:5][CH:6]([N:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][C:15]=2[F:22])[C:9]1=[O:23])[CH3:7]>C(Cl)Cl>[CH3:7][CH:6]([N:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=2[F:22])[C:9]1=[O:23])[CH3:5]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 189810291-(1-Methylethyl)-3-(2-fluoro-4-methoxy-phenyl)imidazolidin-2,4-dione

Produkt 1

HCID 189810733-(2-Fluoro-4-hydroxyphenyl)-1-isopropyl-2,4-imidazolidinedioneAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 1M methylene chloride solution of boron tribromide (41.6 ml, 0.0416 mole) was cooled to -20° C. While this temperature was maintained, a solution of 5.55 g (0.0208 mole) of 1-(1-methylethyl)-3-(2-fluoro-4-methoxyphenyl)imidazolidin-2,4-dione in 25 mL of methylene chloride was added to the reaction during an eight minute period. The reaction mixture was allowed to warm to room temperature, where it was stirred for approximately 17 hours. At the end of this time the reaction was poured over ice, and the resulting two-phase mixture was filtered. The organic phase was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure, leaving a black solid as a residue. This solid was recrystallized from ethyl acetate/petroleum ether, to yield 3.25 g of 1-(1-methylethyl)-3-(2-fluoro-4-hydroxyphenyl)imidazolidin-2,4-dione as a tan solid, m.p. 190°-192° C. The NMR and IR spectra were consistent with the proposed structure.

Aufarbeitung

  1. temperatureWhile this temperature was maintained
  2. additionAt the end of this time the reaction was poured over ice
  3. filtrationthe resulting two-phase mixture was filtered
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customleaving a black solid as a residue
  9. customThis solid was recrystallized from ethyl acetate/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-6603b1c7640f454f8c3995fd6af5bfa2
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262390

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