Benzimidazole → HCID 799461, compound

HRID 897971Notes

Reaction equation

HRID 897971 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-360c78ab58144c3eb6caaff41f2f0a03
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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