2-Aminobenzimidazole → HCID 58362394, Verbindung

HRID 452328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 452328
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[CH:17][CH:16]=1)=[O:14]>CO>[NH2:1][C:2]1[N:6]([CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])=[CH:17][CH:16]=2)=[O:14])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Komponenten

4

Edukt 2

HCID 136242-AminobenzimidazoleHCID 27950302-bromo-1-[4-(diethylamino)phenyl]ethanone

Produkt 1

HCID 58362394HCID 58362394, VerbindungAusbeute 36,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 2-aminobenzimidazole (197 mg, 1.5 mmol) and 2-Bromo-4′-(diethylamino)acetophenone (402 mg, 1.5 mmol) in MeOH (7 mL) was stirred at r.t. for 18 hours. The volatiles were removed in vacuo and NaHCO3 (sat. aq., 30 mL) was added. The aqueous mixture was extracted with EtOAc (3×30 mL). The combined EtOAc extracts were dried with MgSO4 and concentrated in vacuo. The residue was purified on silica gel eluting with a gradient up to 5:95 (MeOH:DCM) to isolate 2-(2-amino-1H-benzo[d]imidazol-1-yl)-1-(4-(diethylamino)phenyl)ethanone (176 mg, 36%) as a beige solid.

Aufarbeitung

  1. customThe volatiles were removed in vacuo and NaHCO3 (sat. aq., 30 mL)
  2. additionwas added
  3. extractionThe aqueous mixture was extracted with EtOAc (3×30 mL)
  4. dry with materialThe combined EtOAc extracts were dried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on silica gel eluting with a gradient up to 5:95 (MeOH:DCM)

Quellen und Nachweise

ORD-Eintrag
ord-cdcdd1d8fd254dbe8e9a6824ff15a654
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08491869B2

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