Methyl iodide → 2-(4-dipropylaminomethyl-phenyl)-3-methyl-3H-benzimidazol-5-carbonitrile

HRID 2080795Notes

Reaction equation

HRID 2080795 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][C:3]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])=[CH:14][CH:13]=1.[H-].[Na+].[CH3:29]I>C1COCC1>[CH2:20]([N:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[N:10]([CH3:29])[C:3]3[CH:4]=[C:5]([C:8]#[N:9])[CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:13][CH:14]=1)[CH2:23][CH2:24][CH3:25])[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23155606N-(2-amino-5-cyano-phenyl)-4-dipropylaminomethyl-benzamide

Product 1

HCID 231553902-(4-dipropylaminomethyl-phenyl)-3-methyl-3H-benzimidazol-5-carbonitrileYield 26.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (613 mg) obtained in Example 29-4 was dissolved in THF (18 ml) and added with 60% sodium hydride (105 mg). After that, the whole was gradually added with methyl iodide (373 mg) and stirred at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform, washed with water, and subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (160 mg) as a brown solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with water
  5. extractionsubjected to extraction with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off
  10. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d64a2e7e0dd5449daf462a96f37f5e7d
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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