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

HRID 482395ノート

反応式

HRID 482395 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 189810733-(2-Fluoro-4-hydroxyphenyl)-1-isopropyl-2,4-imidazolidinedione収率 61.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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-methoxy-phenyl)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.

後処理

  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

出典と根拠

ORDレコード
ord-fc2fb2ed02084d2b8c47b29fb00d1128
出典データセット
uspto-grants-1998_08
特許番号
US05798316

反応ノート

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