Sodium Chloride → 4-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole

HRID 52919Notes

Reaction equation

HRID 52919 reaction equation
[H-].[Na+].[C:3]([C:6]1[N:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH3:16])[NH:9][C:10]=1[C:11]#[N:12])(=[O:5])[CH3:4].Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:26]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:21][CH:20]=1.[Cl-].[Na+]>CN(C)C(=O)C>[C:3]([C:6]1[N:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH3:16])[N:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:21][CH:20]=2)[C:10]=1[C:11]#[N:12])(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178441657HCID 178441657, compound

Product 1

HCID 190361124-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazoleYield 56.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.192 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was added to a solution of 0.843 g of 4-acetyl-2-butylimidazole-5-carbonitrile [prepared as described in Preparation 24(i)] in 17 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 20 minutes. 1.68 g of t-butyl 4'-(bromomethyl)biphenyl-2-carboxylate was then added, and the resulting mixture was stirred at 55° C. for 2.5 hours. At the end of this time, an aqueous solution of sodium chloride was added to the mixture, which was then extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting oily residue was purified by column chromatography through silica gel, using 4:1 and 2:1 by volume mixtures of hexane and ethyl acetate as the eluent, to afford 1.14 g of the title compound as a viscous oil.

Workup

  1. stirringthe resulting mixture was stirred at 55° C. for 2.5 hours
  2. extractionwas then extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe resulting oily residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-9c41600be3824e29ab216e5125863604
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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