Chloroacetone → HCID 66728095, compound

HRID 573338Notes

Reaction equation

HRID 573338 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:21][C:22](=[O:24])[CH3:23]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[N:8]([CH2:21][C:22](=[O:24])[CH3:23])[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 66727956HCID 66727956, compound

Product 1

HCID 66728095HCID 66728095, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-bromophenoxy)-1H-benzo[d]imidazole (5.72 g) in DMF (60 mL) was added NaH (60% in oil, 950 mg) at 0° C. After stirring for 5 min, chloroacetone (2.36 mL) was added to the mixture at 0° C. The mixture was stirred at room temperature for 5 h. The mixture was diluted with AcOEt and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt in hexane) and recrystallized from THF/Et2O to give the title compound (3.47 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 5 h
  2. washwashed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt in hexane)
  7. customrecrystallized from THF/Et2O

Sources & evidence

ORD record
ord-290bae8769424cb5b3b8f655899e1c9f
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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