Methyl iodide → HCID 58529739, compound

HRID 1972756Notes

Reaction equation

HRID 1972756 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.[CH3:20]I>CC(C)=O.C(Cl)Cl>[CH2:3]([C:10]1[N:14]([CH3:20])[C:13]2[CH:15]=[CH:16][C:17]([Br:19])=[CH:18][C:12]=2[N:11]=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 58529739HCID 58529739, compoundYield 37%

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, 18.70 mmol) in acetone (100 mL), after 10 min, methyl iodide (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 filter cake was washed with hexanes and dried on a high vacuum pump to give an off-white solid (2.07 g, 37%). 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. washThe filter cake was washed with hexanes
  6. customdried on a high vacuum pump

Sources & evidence

ORD record
ord-8bbbbe4df0f3471baaa6951f24eaec97
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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