Benzimidazole → 2-benzimidazol-1-yl-N-(4-bromophenyl)-acetamide

HRID 1455616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1455616
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)=[O:4].[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:13]1([CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=2)=[O:4])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1

Komponenten

5

Edukt 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 2255262-Bromo-n-(4-bromophenyl)acetamide

Produkt 1

HCID 170284752-benzimidazol-1-yl-N-(4-bromophenyl)-acetamideAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Bromo-N-(4-bromophenyl)-acetamide (3.083 g, 10.522 mmol), prepared according to J. Med. Chem., 1996, 4(2), 197-203, benzimidazole (1.24 g, 10.52 mmol) and K2CO3 were combined and dissolved in DMF (60 mL) under nitrogen. The reaction mixture was stirred at room temperature overnight before filtering and purifing by SCX cartridge. The crude product thus obtained was washed with EtOAc to remove excess benzimidazole, yielding the pure product (2.20 g, 63% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.17 (2H, s), 7.19-7.28 (2H, m), 7.51 (2H, d, J=12 Hz), 7.51-7.56 (1H, m), 7.57 (2H, d, J=12 Hz), 7.66 (1H, d, J=8 Hz), 8.22 (1H, s), 10.57 (1H, s). MS (ES) m/z: 332.5 [M+H].

Aufarbeitung

  1. filtrationbefore filtering
  2. customThe crude product thus obtained
  3. washwas washed with EtOAc
  4. customto remove excess benzimidazole

Quellen und Nachweise

ORD-Eintrag
ord-63ee8bd55d7d41fba75081141da18398
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482469B2

Notizen zur Reaktion

Wird geladen…