Water → 1-(2-Chloro-1H-benzimidazol-1-yl)propan-2-one

HRID 572180Notes

Reaction equation

HRID 572180 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.[H-].[Na+].Cl[CH2:14][C:15](=[O:17])[CH3:16].O>CN(C=O)C>[Cl:1][C:2]1[N:6]([CH2:14][C:15](=[O:17])[CH3:16])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 785722-Chlorobenzimidazole

Product 1

HCID 122342441-(2-Chloro-1H-benzimidazol-1-yl)propan-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-1H-benzimidazole (1.53 g) in DMF (20 ml) was added sodium hydride (60% in oil, 0.480 g) at 0° C. by small portions. After stirring for 10 min, chloroacetone (1.19 mL) was added, and the obtained mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) and recrystallized from ethyl acetate to give the title compound (1.73 g).

Workup

  1. stirringthe obtained mixture was stirred at room temperature for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a87a37eab922407da788b80a20a1eefe
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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