Potassium Carbonate → 2-Chloro-1-(4-methoxybenzyl)-1H-benzo[D]imidazole

HRID 410212Notes

Reaction equation

HRID 410212 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 785722-Chlorobenzimidazole

Product 1

HCID 110330152-Chloro-1-(4-methoxybenzyl)-1H-benzo[D]imidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a round bottomed flask was added 2-chloro-1H-benzo[d]imidazole (1.000 g, 6.55 mmol), 1-(chloromethyl)-4-methoxybenzene (1.540 g, 9.83 mmol), and potassium carbonate (1.359 g, 9.83 mmol) in DMF (21.85 mL) to stir overnight. Reaction was allowed to cool to room temperature. The reaction mixture was diluted with water and extracted with DCM. The organic extract was washed with water, brine, dried with magnesium sulfate, filtered, and concentrated to provide 2-Chloro-1-(4-methoxybenzyl)-1H-benzo[d]imidazole. MS (ESI, pos. ion) m/z: 273.2 (M+1).

Workup

  1. customReaction
  2. extractionextracted with DCM
  3. extractionThe organic extract
  4. washwas washed with water, brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fb5c6e44977f4bc9b39c0d6f11915443
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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