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

HRID 1455616Notes

Reaction equation

HRID 1455616 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 170284752-benzimidazol-1-yl-N-(4-bromophenyl)-acetamideYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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].

Workup

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

Sources & evidence

ORD record
ord-63ee8bd55d7d41fba75081141da18398
Source dataset
uspto-grants-2009_01
Patent number
US07482469B2

Reaction notes

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