Sodium hydride → Diethyl [2-n-butyl-1-{(2-chlorophenyl)methyl}-1h-imidazol-5-yl]-2-benzylmalonate

HRID 377676

Reaction equation

HRID 377676 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].Cl.[CH2:22]([C:26]1[N:27]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])[C:28](CCl)=[CH:29][N:30]=1)[CH2:23][CH2:24][CH3:25]>CN(C)C=O>[CH2:22]([C:26]1[N:27]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])[C:28]([C:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:6]([O:5][CH2:4][CH3:3])=[O:7])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:29][N:30]=1)[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 69090Diethyl 2-benzylpropanedioateHCID 193515432-n-butyl-1-(2-chlorophenyl)methyl-5chloromethyl-1H-imidazole hydrochloride

Product 1

HCID 57500985Diethyl [2-n-butyl-1-{(2-chlorophenyl)methyl}-1h-imidazol-5-yl]-2-benzylmalonateYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To dry dimethylformamide (50 mL) under argon was added sodium hydride (0.53 g, 0.022 mol) followed by diethyl benzyl malonate (5.51 g, 0.022 mol) in dimethylformamide (10 mL) at 0° C. The mixture was stirred at ambient temperature for one hour. A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-5-chloromethyl-1H-imidazole hydrochloride (3.5 g, 0.0105 mol) in dimethylformamide (40 mL) was added over 5 minutes. The reaction mixture was stirred at 25° C. for 18 hours, then partitioned between water and methylene chloride. The organic layer was washed with water, dried, and concentrated. The crude product was flash chromatographed over silica gel to give 4.54 g (85%) of the title compound as an oil.

Workup

  1. stirringThe reaction mixture was stirred at 25° C. for 18 hours
  2. custompartitioned between water and methylene chloride
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed over silica gel

Sources & evidence

ORD record
ord-c93fa601fb794b54b5c049676e5d2c09
Source dataset
uspto-grants-2000_02
Patent number
US06028091

Linked notes

Loading…