Hydroxyamine hydrochloride → (NE)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methylidene]hydroxylamine

HRID 2113445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2113445
[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1/[CH:4]=[N:16]/[OH:17]

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 27833242-Fluoro-5-(trifluoromethoxy)benzaldehyde

Produkt 1

HCID 87441576(NE)-N-[[2-fluoro-5-(trifluoromethoxy)phenyl]methylidene]hydroxylamineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-fluoro-5-trifluoromethoxy-benzaldehyde (9.78 g, 47 mmol) in ethanol (50 ml) was treated with hydroxylamine HCl (3.59 g, 52 mmol) and sodium acetate (4.27 g, 52 mmol). The mixture was refluxed for 2 h, the solvent was evaporated and the residue stirred with water (50 ml). The precipitate was filtered, dried and chromatographed (SiO2, heptanes:Ethyl acetate=100:0 to 80:2) and afforded the title compound (9.21 g, 88%) as a white solid. MS: m/e=223.0 [M]+.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 h
  2. customthe solvent was evaporated
  3. filtrationThe precipitate was filtered
  4. customdried
  5. customchromatographed (SiO2, heptanes:Ethyl acetate=100:0 to 80:2)

Quellen und Nachweise

ORD-Eintrag
ord-e109772573ec401c8cd74992df4e923f
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432256B2

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