Dimethylformamide → 1-[6-(4-Bromophenoxy)hexyl]-4-phenyl-3-(4-pyridyl)-2-imidazolidinone

HRID 49272Notes

Reaction equation

HRID 49272 reaction equation
[C:1]1([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[C:10](=NC#N)[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=1.CN(C=[O:42])C>>[Br:37][C:34]1[CH:35]=[CH:36][C:31]([O:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][N:9]2[CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:11]([C:12]3[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=3)[C:10]2=[O:42])=[CH:32][CH:33]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 224947501-Bromo-4-((6-bromohexyl)oxy)benzeneHCID 178512069[5-phenyl-1-(4-pyridyl)tetrahydro-1H-2-imidazolyliden]aminomethane-nitrile

Product 1

HCID 103112281-[6-(4-Bromophenoxy)hexyl]-4-phenyl-3-(4-pyridyl)-2-imidazolidinone

Procedure

To a solution of [5-phenyl-1-(4-pyridyl)tetrahydro-1H-2-imidazolyliden] aminomethane-nitrile (0.1 g, 0.38 mmol) in 6 mL of DMF at 0° C. was added sodium hydride (75% dispersion in mineral oil, 24 mg) in one portion. The mixture was stirred at room temperature for 20 min and then 1-[(6-bromohexyl)oxy]-4-bromobenzene (192 mg, 0.57 mmol) dissolved in DMF (4 mL) was added dropwise. The resulting mixture was stirred and heated at 80° C. for 16 hours. The reaction was quenched with water and aqueous solution was extracted with ether (3×20 mL). The organic layers were combined, washed with NaCl(sat.), dried over MgSO4, and concentrated under reduced pressure to give the crude residue, which was subjected to purification by chromatography elution with ethyl acetate and methanol (20:1) to afford the product (i.e., Compound 15) as a white solid (90 mg, 45%).

Workup

  1. additionwas added dropwise
  2. stirringThe resulting mixture was stirred
  3. temperatureheated at 80° C. for 16 hours
  4. customThe reaction was quenched with water and aqueous solution
  5. extractionwas extracted with ether (3×20 mL)
  6. washwashed with NaCl(sat.)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customto give the crude residue, which
  10. customwas subjected to purification by chromatography elution with ethyl acetate and methanol (20:1)

Sources & evidence

ORD record
ord-6ea8d5dd868d4ea28cb4edcfc909677c
Source dataset
uspto-grants-2004_03
Patent number
US06706739B2

Reaction notes

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