Benzimidazole → HCID 799461, compound

HRID 2056148Notes

Reaction equation

HRID 2056148 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][CH:3]=1.[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[CH:11]1.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 685274-Bromobenzyl bromide

Product 1

HCID 799461HCID 799461, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
139 °C

Procedure

1-Bromo-4-(bromomethyl)benzene (2.50 g, 10 mmol), 1H-benzo[d]imidazole (1.181 g, 10.0 mmol), potassium hydroxide (0.561 g, 10.0 mmol), potassium carbonate (1.382 g, 10.0 mmol) and tetrabutylammonium bromide (0.161 g, 0.5 mmol) was mixed in xylenes (60 mL). The reaction mixture was heated at 139° C. overnight. The hot reaction mixture was filtered and washed with hot xylenes. The solvent was evaporated and the residue was purified by flash column chromatography using dichloromethane/methanol (95:5 to 80:20) as mobile phase to give 1-(4-Bromobenzyl)-1H-benzo[d]imidazole (1.193 g, 42%). 1H NMR (CDCl3) δ 5.31 (s, 2H), 7.05 (m, 2H), 7.28 (m, 3H), 7.46 (m, 2H), 7.82 (m, 1H), 7.95 (s, 1H).

Workup

  1. filtrationThe hot reaction mixture was filtered
  2. washwashed with hot xylenes
  3. customThe solvent was evaporated
  4. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-00ebbe34a1c746ceb80d7248edf66e98
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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