Methyl iodide → HCID 58529665, compound

HRID 1972755Notes

Reaction equation

HRID 1972755 reaction equation
[OH-].[K+].[CH2:3]([C:10]1[NH:14][C:13]2[CH:15]=[CH:16][C:17]([Br:19])=[CH:18][C:12]=2[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH3:21]>CC(C)=O.C(Cl)Cl>[CH2:3]([C:10]1[N:11]([CH3:21])[C:12]2[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:13]=2[N:14]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178419325HCID 178419325, compound

Product 1

HCID 58529665HCID 58529665, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

Powdered KOH (5.25 g, 93.50 mmol) was added to a stirred solution of 2-benzyl-5-bromo-1H-benzimidazole (5.37 g, 8.70 mmol) in acetone (100 mL), after 10 min, iodomethane (1.28 mL, 20.57 mmol) was added and the mixture was stirred for 1 h and diluted with DCM. The mixture was washed with water and brine, then dried over Na2SO4 and concentrated. The residue was taken up in DCM and hexanes and the resulting suspension filtered. The filtrate was concentrated and the oily residue taken up in hexanes and stirred for about 1 h. The resulting solid was filtered and the filter cake washed with hexanes and dried (2.0 g, 34%). LC-MS [M+H]+=302.1, RT=2.47 min.

Workup

  1. washThe mixture was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. filtrationhexanes and the resulting suspension filtered
  5. concentrationThe filtrate was concentrated
  6. stirringstirred for about 1 h
  7. filtrationThe resulting solid was filtered
  8. washthe filter cake washed with hexanes
  9. customdried (2.0 g, 34%)

Sources & evidence

ORD record
ord-51e65a748c104f70b83c33cd28e9b1d1
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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