Hydroxylamine → HCID 178448432, Verbindung

HRID 1966762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966762
[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:7]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]#[N:12])=[N:8][C:4]=2[CH:3]=1.[NH2:23][OH:24]>CCO>[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:17]([CH3:18])([CH3:19])[CH3:20])[C:7]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]([NH:23][OH:24])=[NH:12])=[N:8][C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 787HydroxylamineHCID 58542011HCID 58542011, Verbindung

Produkt 1

HCID 178448432HCID 178448432, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-benzonitrile (765 mg, 2.16 mmol) in EtOH (15 mL) is added hydroxylamine 50% aqueous solution (2.85 mL, 43.19 mmol) at room temperature. The solution is heated to 80° C. for 2 hours. The reaction mixture is cooled to room temperature and the ethanol removed in vacuo. Water (30 mL) is added to the reaction mixture and the resultant precipitate is filtered and washed with 10% EtOAc/heptane (10 mL) to afford 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-N-hydroxy-benzamidine (716 mg, 81%).

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe ethanol removed in vacuo
  3. additionWater (30 mL) is added to the reaction mixture
  4. filtrationthe resultant precipitate is filtered
  5. washwashed with 10% EtOAc/heptane (10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-8631b78c487a43aaa55115e2ec4e8469
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420655B2

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