Ammonium Acetate → (1,4-bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-acetic acid ethyl ester

HRID 1428941Notes

Reaction equation

HRID 1428941 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]([N:8]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=O)=O)[CH3:2].C([O-])(=O)C.[NH4+:31]>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[N:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:31]=1)[CH3:2]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 86687939N-(4-fluoro-phenyl)-N-(2-(4-fluoro-phenyl)-2-oxo-ethyl)-malonamic acid ethyl ester

Product 1

HCID 86687938(1,4-bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-acetic acid ethyl esterYield 8.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.2 g N-(4-fluoro-phenyl)-N-(2-(4-fluoro-phenyl)-2-oxo-ethyl)-malonamic acid ethyl ester and 1.8 g ammonium acetate in 20 mL concentrated acetic acid were refluxed 4 h. The reaction was evaporated. Water was added to the residue and the mixture was extracted with DCM. The organic layer was dried and evaporated. The residue was purified by chromatography on silica (100% dichlormethane) to yield 100 mg of the desired compound. Rt: 1.39 min (method B), (M+H)+: 343

Workup

  1. customThe reaction was evaporated
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with DCM
  4. customThe organic layer was dried
  5. customevaporated
  6. customThe residue was purified by chromatography on silica (100% dichlormethane)

Sources & evidence

ORD record
ord-56941b4d3859417e8a31a7741b6efb46
Source dataset
uspto-grants-2015_01
Patent number
US08937176B2

Reaction notes

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