Ethanone, 1-(2,4,6-trimethylphenyl)- → 8-Chloro-5-(1-ethylpropyl)-1-[(2,4,6-trimethylphenyl)carbonyl]-2,3-dihydro-1h-imidazo[1,2-a]benzimidazole

HRID 1399142Notes

Reaction equation

HRID 1399142 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[NH:11][CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([C:29](C)=[O:30])=[C:24]([CH3:32])[CH:23]=1>CN(C)C=O.O>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:29]([C:25]4[C:24]([CH3:32])=[CH:23][C:22]([CH3:21])=[CH:27][C:26]=4[CH3:28])=[O:30])[CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 15461Ethanone, 1-(2,4,6-trimethylphenyl)-HCID 24758Sodium hydrideHCID 1360477328-Chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole

Product 1

HCID 577862868-Chloro-5-(1-ethylpropyl)-1-[(2,4,6-trimethylphenyl)carbonyl]-2,3-dihydro-1h-imidazo[1,2-a]benzimidazoleYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (32.9 mg, 0.125 mmol) in N,N-dimethylformamide (0.5 mL) was added sodium hydride (19.8 μL, 0.142 mmol) at 0° C. After 15 min, to the mixture was added 2,4,6-trimethylacetophenone (27.2 mg, 0.149 mmol). The reaction mixture was stirred at room temperature for 18 hrs. The mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic layer was washed and brine (×1), dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-30% ethyl acetate/n-hexane gradient mixture. The resulting solid was recrystallized from n-hexane to give the title compound as a pale pink powder (24.0 mg, 0.0585 mmol, 47%).

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washThe combined organic layer was washed
  3. dry with materialbrine (×1), dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with a 0-30% ethyl acetate/n-hexane gradient mixture
  7. customThe resulting solid was recrystallized from n-hexane

Sources & evidence

ORD record
ord-3c5ddef70e90459892e13cc259d8d77f
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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