Methyl iodide → HCID 23094064, compound

HRID 1850032Notes

Reaction equation

HRID 1850032 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.I[CH3:18].[H-].[Na+]>CN(C=O)C>[CH3:18][N:12]1[C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4905889HCID 4905889, compound

Product 1

HCID 23094064HCID 23094064, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Iodophenyl)benzimidazole (200 mg, 0.6 mmol) was methylated with iodomethane (180 mg, 1.2 mmol, 2.0 eq.) and NaH (45 mg, 1.8 mmol, 3 eq.) in DMF (3 mL) for 18 h. Dilution with diethyl ether, washing with water, drying over Na2SO4, and chromatography (10→25% EtOAc/hexanes) gave 1-methyl-2-(4-iodophenyl)benzimidazole (124 mg, 59%).

Workup

  1. washDilution with diethyl ether, washing with water
  2. dry with materialdrying over Na2SO4, and chromatography (10→25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-054d6e2668f24bf1b0a05835b3f690ae
Source dataset
uspto-grants-2015_02
Patent number
US08957049B2

Reaction notes

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