Isobutyl iodide → HCID 22393695, compound

HRID 553450Notes

Reaction equation

HRID 553450 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C([O-])([O-])=O.[K+].[K+].[CH2:17](I)[CH:18]([CH3:20])[CH3:19]>CN(C=O)C>[Cl:1][C:2]1[N:6]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 10556Isobutyl iodideHCID 11430Potassium CarbonateHCID 785722-Chlorobenzimidazole

Product 1

HCID 22393695HCID 22393695, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-benzoimidazole (1.0 eq.) in DMF was added K2CO3 (2.0 eq.) and isobutyl iodide (1.5 eq.). The reaction mixture was stirred at room temperature for 3 days. The reaction mixture was poured into ice-water. The mixture was extracted with ethyl acetate (3×100 mL), washed with brine, dried over Na2SO4, concentrated to get a residue, which was purified by column chromatography to afford 4 g (96%) of 2-chloro-1-isobutyl-benzoimidazole.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto get a residue, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b5ba9840417c43eca09345b67085ec32
Source dataset
uspto-grants-2011_11
Patent number
US08048862B2

Reaction notes

Loading…