Methyl iodide → HCID 21800722, compound

HRID 2379128Notes

Reaction equation

HRID 2379128 reaction equation
[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][C:10]=3[N:9]=[CH:8]2)[CH:2]=1.[H-].[Na+].I[CH3:27]>CN(C=O)C.O>[C:1]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([CH2:16][O:17][CH3:27])=[CH:15][C:10]=3[N:9]=[CH:8]2)[CH:2]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18957882HCID 18957882, compound

Product 1

HCID 21800722HCID 21800722, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1--(3-biphenylyl)-5-hydroxymethylbenzimidazole (61a) (0.16 g, 0.5 mmol) in dry DMF (1.5 ml) under nitrogen, was added a 80% sodium hydride suspension (20 mg, 0.7 mmol) and then iodomethane (33.5 μl, 0.5 mmol). The reaction mixture was stirred overnight and then poured in water. Neutralization with 4M aqueous HCl was followed by extraction with ethyl acetate. The extract was evaporated to dryness and purified by chromatography. The product was dissolved in dry ether and precipitated as the hydrochloride. Yield: 130 mg, 0.4 mmol, 80%. mp 70°-72° C.

Workup

  1. extractionNeutralization with 4M aqueous HCl was followed by extraction with ethyl acetate
  2. customThe extract was evaporated to dryness
  3. custompurified by chromatography
  4. dissolutionThe product was dissolved in dry ether
  5. customprecipitated as the hydrochloride

Sources & evidence

ORD record
ord-644a16675c154c2fbcbfe8d0676d7217
Source dataset
uspto-grants-1994_11
Patent number
US05360809

Reaction notes

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