Hydroxyamine hydrochloride → HCID 135961542, Verbindung

HRID 2353386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353386
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5](/[C:9](/[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[N:10]\NC(OC(C)(C)C)=O)=[C:4]([F:25])[CH:3]=1.Cl.NO.C([O-])(=[O:31])C.[Na+]>C(O)C.O>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[N:10][OH:31])=[C:4]([F:25])[CH:3]=1

Komponenten

6

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 145724999HCID 145724999, Verbindung2×

Produkt 1

HCID 135961542HCID 135961542, VerbindungAusbeute 114,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of Z/E 1-(4-bromo-2,5-difluorophenyl)-1-(4-pyridinyl)methanimine (Intermediate 1, 150 mg) in ethanol (2 ml) was treated with a solution of hydroxylamine hydrochloride (44 mg) and sodium acetate (50 mg) in water (0.4 ml) then stirred at reflux for 2 h. The ethanol was removed under vacuum and the residue was partitioned between water and ethyl acetate. The aqueous layer was re-extracted with ethyl acetate and the combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated under vacuum. The residue was purified on an SPE cartridge (silica, 2 g) eluting with cyclohexane/ethyl acetate (4:1 to 1:1) to give the title compound as a white foam (130 mg).

Aufarbeitung

  1. temperatureat reflux for 2 h
  2. customThe ethanol was removed under vacuum
  3. customthe residue was partitioned between water and ethyl acetate
  4. extractionThe aqueous layer was re-extracted with ethyl acetate
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified on an SPE cartridge (silica, 2 g)
  9. washeluting with cyclohexane/ethyl acetate (4:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-079580893551434a8e377b673dc9e15c
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750026B2

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