Hydroxyamine hydrochloride → 1-[3-bromo-2-(tert-butylsulfanyl)phenyl]-N-hydroxymethanimine

HRID 389437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389437
[Br:1][C:2]1[C:3]([S:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.Cl.[NH2:16][OH:17]>CC(O)C.O>[Br:1][C:2]1[C:3]([S:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH:5]=[N:16][OH:17])[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 866623973-Bromo-2-(tert-butylthio)benzaldehyde

Produkt 1

HCID 866623981-[3-bromo-2-(tert-butylsulfanyl)phenyl]-N-hydroxymethanimine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
67.5 °C

Versuchsvorschrift

A mixture of 3-bromo-2-tert-butylsulfanyl-benzaldehyde (6.7 g, 25 mmol) and hydroxylamine hydrochloride (7.9 g, 116 mmol) in 2-propanol (200 mL) and water (40 mL) was heated to 65-70° C. overnight. 2-Propanol was evaporated and water (150 mL) was added to the residue followed by saturated aqueous sodium bicarbonate to bring the pH to ˜8.5. The mixture was extracted with DCM (3×80 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated to afford the title compound, which was used immediately without further purification. 1H NMR (300 MHz, CD3OD): δ 1.28 (s, 9H), 7.25-7.35 (t, J=7.8 Hz, 1H), 7.79 (d, J=6.6 Hz, 1H), 7.89 (d, J=6.3 Hz, 1H), 8.83 (s, 1H).

Aufarbeitung

  1. custom2-Propanol was evaporated
  2. additionwater (150 mL) was added to the residue
  3. extractionThe mixture was extracted with DCM (3×80 mL)
  4. dry with materialThe combined organic fractions were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1c5ca2ddc72f4b629ae272aa4eecacfc
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378104B2

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