Benzimidazole → HCID 799461, compound

HRID 1716862Notes

Reaction equation

HRID 1716862 reaction equation
[H-].[Na+].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH:4]=1.[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1>CN(C=O)C>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[CH:4]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromide

Product 1

HCID 799461HCID 799461, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (60% in mineral oil, 1.86 g, 46.6 mmol) in dry DMF (5 mL) under nitrogen and cooled to 0° C. was added a solution of benzimidazole (5.0 g, 42.2 mmol) in DMF (15 mL) and the reaction mixture was allowed to stir for 30 min at room temperature. The reaction mixture was cooled to 0° C. and a solution of 4-bromobenzyl bromide (10.6 g, 42.4 mmol) in DMF (10 mL) was added dropwise and the reaction mixture was allowed to warm to room temperature overnight. The solvent was removed under reduced pressure and the residue partitioned between saturated aqueous sodium chloride and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (Na2SO4) and evaporated. The crude product was triturated with ethyl ether and recovered by filtration. Yield: 70%. LCMS (ESI+) 387.2 and 389.2 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperatureto warm to room temperature overnight
  3. customThe solvent was removed under reduced pressure
  4. customthe residue partitioned between saturated aqueous sodium chloride and ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe crude product was triturated with ethyl ether
  9. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-f936a2b2c0a64e4fb2b8a73be5277685
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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