Methyl iodide → HCID 69595825, compound

HRID 1796514Notes

Reaction equation

HRID 1796514 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[CH:13][C:8]=3[N:7]=[C:6]2[CH:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=2)[CH3:19])[CH2:3][CH2:2]1.[H-].[Na+].I[CH3:32]>C1COCC1>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([N:14]([CH3:32])[C:15](=[O:17])[CH3:16])=[CH:13][C:8]=3[N:7]=[C:6]2[CH:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=2)[CH3:19])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22181428HCID 22181428, compound

Product 1

HCID 69595825HCID 69595825, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[1-(cyclopropylmethyl)-2-[1-(4-ethoxyphenyl)ethyl]-1H-benzimidazol-5-yl]-acetamide (2.13 g, 5.64 mmol) in THF (100 mL) was added NaH (0.45 g, 11.28 mmol) at 0° C. After stirring for 2 h, iodomethane (1.60 g, 11.28 mmol) was added at room temperature. The mixture was stirred overnight, quenched with MeOH (2 mL) and diluted with ether (200 mL) which was washed with saturated solution of ammonium chloride (100 mL) and dried with Na2SO4. After filtration and evaporation, the title compound (2.43 g, 100%) as a crude product was obtained. MS (ES) (M+H)+=392.40.

Workup

  1. stirringThe mixture was stirred overnight
  2. customquenched with MeOH (2 mL)
  3. additiondiluted with ether (200 mL) which
  4. washwas washed with saturated solution of ammonium chloride (100 mL)
  5. dry with materialdried with Na2SO4
  6. filtrationAfter filtration and evaporation

Sources & evidence

ORD record
ord-677c428ebdb54a508c18ad2cbdb02d89
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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