Ethyl bromoacetate → Ethyl 4,5-diphenyl-1H-imidazole-1-acetate

HRID 1088294

Reaction equation

HRID 1088294 reaction equation
[H-].[Na+].[C:3]1([C:9]2[N:10]=[CH:11][NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C=O)C>[C:3]1([C:9]2[N:10]=[CH:11][N:12]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:13]=2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 695884,5-Diphenylimidazole

Product 1

HCID 14820171Ethyl 4,5-diphenyl-1H-imidazole-1-acetateYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 9.6 (0.24 mol) of 60% sodium hydride-mineral oil in 100 mL of DMF under nitrogen at 0° C. was added dropwise 50.0 g (0.226 mol) of 4,5-diphenylimidazole in 400 mL DMF. The mixture was allowed to warm, stirred at room temperature 1 hr, and 26.6 mL (0.24 mol) of ethyl bromoacetate was added. The reaction was stirred 18 hr at room temperature, heated on a steam bath 2 hr, cooled, and stripped. The residue was partitioned between water and methylene chloride, dried over MgSO4, and filtered through a silica gel column eluting with methylene chloride-ethyl acetate to provide 50.1 g of an oil that solidified on standing. It may be used in further reactions as is, or it may be recrystallized from ether to yield 35.1 g of product mp 89°-90° C.

Workup

  1. temperatureto warm
  2. stirringThe reaction was stirred 18 hr at room temperature
  3. temperatureheated on a steam bath 2 hr
  4. temperaturecooled
  5. customThe residue was partitioned between water and methylene chloride
  6. dry with materialdried over MgSO4
  7. filtrationfiltered through a silica gel column
  8. washeluting with methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-3685b654f7e5464c9714549d37a65270
Source dataset
uspto-grants-1990_10
Patent number
US04962120

Linked notes

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