Hydrogen Peroxide → N-(4-bromo-2-fluorophenyl)-5,7-dimethylbenzo[d]oxazol-2-amine

HRID 885103

反応式

HRID 885103 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[F:11][C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=1[N:19]=[C:20]=S.O[Li].O.OO>O1CCCC1>[Br:18][C:16]1[CH:15]=[CH:14][C:13]([NH:19][C:20]2[O:10][C:3]3[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[N:1]=2)=[C:12]([F:11])[CH:17]=1

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 1005306-Amino-2,4-xylenolHCID 168937Lithium hydroxide, monohydrateHCID 27570034-Bromo-2-fluorophenylisothiocyanate

生成物 1

HCID 22347267N-(4-bromo-2-fluorophenyl)-5,7-dimethylbenzo[d]oxazol-2-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

An ambient solution of 2-amino-4,6-dimethylphenol (0.85 g, 6.2 mmol) and 2-fluoro-4-bromophenyl isothiocyanate (1.44 g, 6.20 mmol) in tetrahydrofuran (20 mL) was stirred for 16 h. The reaction was cooled (0° C.), and LiOH.H2O (0.521 g, 12.41 mmol) was added, followed by the dropwise addition of 30% H2O2 (3.41 mL, 31.0 mmol) over 15 minutes. The reaction was warmed to room temperature and stirred for 16 h. The reaction was then quenched by the addition of 20% aqueous sodium sulfite solution (50 mL) and ethyl acetate (75 mL). The layers were separated, and the aqueous was extracted with additional ethyl acetate (2×75 mL). The combined organics were, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 gel, eluting with 25% ethyl acetate in hexane, to give the title compound. MS (ESI) m/z 335[M+H]+.

後処理

  1. additionwas added
  2. customThe reaction was then quenched by the addition of 20% aqueous sodium sulfite solution (50 mL) and ethyl acetate (75 mL)
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with additional ethyl acetate (2×75 mL)
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on SiO2 gel
  9. washeluting with 25% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-ddde47f43ef44ce28af6c7bb74a78a96
出典データセット
uspto-grants-2012_08
特許番号
US08242139B2

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