Sodium hydride → 3-(4-Chlorobenzyl)-5-[2-(4-methylpiperazin-1-yl)-benzylidene]-imidazolidine-2,4-dione

HRID 896993Notes

Reaction equation

HRID 896993 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[C:13](=[O:14])[CH2:12][NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1.[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=O)[CH2:21][CH2:20]1>O1CCCC1>[Cl:3][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[C:13](=[O:14])[C:12](=[CH:27][C:26]3[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=3[N:22]3[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]3)[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10851902,4-Imidazolidinedione, 3-[(4-chlorophenyl)methyl]-HCID 27955662-(4-Methylpiperazin-1-yl)benzaldehyde

Product 1

HCID 539732983-(4-Chlorobenzyl)-5-[2-(4-methylpiperazin-1-yl)-benzylidene]-imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere in a flame-dried flask, sodium hydride (43 mg, 1.07 mmol, 60% oil dispersion) was washed with hexanes and then treated with tetrahydrofuran (THF) (8 mL), followed by 3-(4-chlorobenzyl)-imidazolidine-2,4-dione (235 mg, 1.04 mmol) and 2-(4-methylpiperazin-1-yl)-benzaldehyde (209 mg, 1.02 mmol), and an additional 2 mL of THF. After refluxing the mixture overnight, the solvent was removed and the residue was treated with aqueous ammonium chloride and aqueous sodium bicarbonate to a pH of 8, then extracted with methylene chloride. The organic extracts were washed with aqueous sodium chloride, dried and concentrated in vacuo to a yellow foam. The foam was crystallized from hot ethyl acetate: hexanes to give a solid, 240 mg (57%).

Workup

  1. temperatureAfter refluxing the mixture overnight
  2. customthe solvent was removed
  3. additionthe residue was treated with aqueous ammonium chloride and aqueous sodium bicarbonate to a pH of 8
  4. extractionextracted with methylene chloride
  5. washThe organic extracts were washed with aqueous sodium chloride
  6. customdried
  7. concentrationconcentrated in vacuo to a yellow foam
  8. customThe foam was crystallized from hot ethyl acetate
  9. customhexanes to give a solid, 240 mg (57%)

Sources & evidence

ORD record
ord-4e7c6178bc354123ad7cd30a79b85db3
Source dataset
uspto-grants-2005_07
Patent number
US06921760B2

Reaction notes

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