Methyl iodide → 4-[1-(3,5-Dichlorophenyl)-3-methyl-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile

HRID 488737Notes

Reaction equation

HRID 488737 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3=[CH:14][CH2:15][CH2:16][CH2:17][C:12]3([CH2:18][C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)[NH:11][C:10]2=[O:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].[CH3:30]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3=[CH:14][CH2:15][CH2:16][CH2:17][C:12]3([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=3)[N:11]([CH3:30])[C:10]2=[O:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 104534514-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile

Product 1

HCID 103415824-[1-(3,5-Dichlorophenyl)-3-methyl-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (200 mg) (0.5 mmol) in DMF (6 ml) was carefully dropped on a suspension of NaH 60% (24.1 mg) (1.2 eq) in DMF (5 ml) at RT. The reaction mixture was stirred 1 h at RT then methyl iodide (0.095 ml) (3 eq) was added. After one night, the reaction mixture was poured on water and extracted with tBuOMe. The organic layer was washed with water, dried over Na2SO4, and concentrated to yield a solid which was washed with diisopropyl ether to give 4-[1-(3,5-Dichlorophenyl)-3-methyl-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (115 mg) as a white solid. 1H NMR (CDCl3): 7.55 (2H, d), 7.25 (2H, d), 7.10 (1H, m), 6.75 (2H, m), 4.95 (1H, m), 3.10-3.0 (5H, m), 2.45-1.65 (6H, m).

Workup

  1. waitAfter one night
  2. additionthe reaction mixture was poured on water
  3. extractionextracted with tBuOMe
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto yield a solid which
  8. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-8f88198e26e446a3ab9a21af85393dbb
Source dataset
uspto-grants-2005_12
Patent number
US06974815B2

Reaction notes

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