Iodoethane → HCID 10477528, compound

HRID 488740Notes

Reaction equation

HRID 488740 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+].[CH2:30](I)[CH3:31]>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]([CH2:30][CH3:31])[C:10]2=[O:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 104534514-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile

Product 1

HCID 10477528HCID 10477528, compound

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 (150 mg) (0.38 mmol) in DMF (5 ml) was carefully dropped on a suspension of NaH 60% (18.2 mg) (1.2 eq) in DMF (5 ml) at RT. The reaction mixture was stirred 1 h at RT, then ethyl iodide (0.046 ml) (1.5 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 purified by HPLC to give 4-[1-(3,5-Dichlorophenyl)-3-ethyl-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (18.2 mg) as a white solid. 1H NMR (CDCl3):. 7.55 (2H, d), 7.25 (2H, d), 7.10 (1H, m), 6.80 (2H, m), 4.95 (1H, m), 3.75 (1H, m), 3.15 (1H, m), 3.0 (2H, s), 2.5-1.7 (6H, m), 1.25 (3H, t).

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. customwas purified by HPLC

Sources & evidence

ORD record
ord-6168f262f4de4fdf98294e9ad8357924
Source dataset
uspto-grants-2005_12
Patent number
US06974815B2

Reaction notes

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