Methyl iodide → 7-(3-(1-Methoxyethyl)Phenyl)-1-phenyl-5-trifluoromethylbenzimidazole

HRID 644536Notes

Reaction equation

HRID 644536 reaction equation
[OH:1][CH:2]([C:4]1[CH:5]=[C:6]([C:10]2[C:15]3[N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:17]=[N:18][C:14]=3[CH:13]=[C:12]([C:25]([F:28])([F:27])[F:26])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].[H-].[Na+].[H][H].I[CH3:34]>CN(C=O)C.O>[CH3:34][O:1][CH:2]([C:4]1[CH:5]=[C:6]([C:10]2[C:15]3[N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:17]=[N:18][C:14]=3[CH:13]=[C:12]([C:25]([F:28])([F:27])[F:26])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11372470HCID 11372470, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 113384407-(3-(1-Methoxyethyl)Phenyl)-1-phenyl-5-trifluoromethylbenzimidazoleYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 7-(3-(1-hydroxyethyl)phenyl)-1-phenyl-5-trifluoromethylbenzimidazole (0.9 g, 2.4 mmol) in anhydrous DMF (5 ml) was added sodium hydride (0.15 g 60% dispersion in mineral oil, 3.5 mmol) at ambient temperature. When the evolution of hydrogen had ceased iodomethane (0.25 ml, 2.6 mmol) was added and stirring was continued for 15 min. Four volumes of water was added and the resultant mixture was extracted with ethyl acetate. This extract was washed twice with aqueous calcium chloride (3M), dried over magnesium sulphate and evaporated under reduced pressure. The residue was eluted through silica gel with a mixture of ethyl acetate and petroleum ether (2:3, v/v). Trituration of the concentrated eluate in ligroin afforded the title product (0.35 g, 37%) m/z, 397.2 (M+H)+.

Workup

  1. additionwas added
  2. extractionthe resultant mixture was extracted with ethyl acetate
  3. washThis extract was washed twice with aqueous calcium chloride (3M)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. washThe residue was eluted through silica gel with a mixture of ethyl acetate and petroleum ether (2:3

Sources & evidence

ORD record
ord-a758a711e4b74f5eb843d5e8610b26be
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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