1,3-Dibromopropane → 5-(3-bromopropoxy)-1H-benzo[d]imidazol-2(3H)-one

HRID 1750111Notes

Reaction equation

HRID 1750111 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[Br:12][CH2:13][CH2:14][CH2:15]Br.C([O-])([O-])=O.[K+].[K+]>CCO>[Br:12][CH2:13][CH2:14][CH2:15][O:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 136166402H-Benzimidazol-2-one, 1,3-dihydro-5-hydroxy-

Product 1

HCID 666336885-(3-bromopropoxy)-1H-benzo[d]imidazol-2(3H)-oneYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of intermediate 38 (5 g, 33.3 mmol), 1,3-dibromopropane (4 mL, 33.3 mmol) and anhydrous K2CO3 (4.6 g, 33.3 mmol) in EtOH (25 mL) was heated to reflux and stirred overnight. The solvent was removed under vacuum. The residue was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with water, brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH=100:1) to give 5-(3-bromopropoxy)-1H-benzo[d]imidazol-2(3H)-one (intermediate 39) (240 mg, 12%) as a yellow solid.

Workup

  1. temperatureto reflux
  2. customThe solvent was removed under vacuum
  3. additionThe residue was diluted with water
  4. extractionextracted with EtOAc
  5. washThe combined EtOAc layers were washed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH=100:1)

Sources & evidence

ORD record
ord-9a1870c889f949b2ad25537370583c92
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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