2-Bromo-1-[4-(trifluoromethoxy)phenyl]ethan-1-one → N-[4-(4-Trifluoromethoxy-phenyl)-1H-imidazol-2-yl]-acetamide

HRID 1695200Notes

Reaction equation

HRID 1695200 reaction equation
[C:1]([NH:4][C:5]([NH2:7])=[NH:6])(=[O:3])[CH3:2].Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1)=O>CN(C=O)C>[F:20][C:19]([F:21])([F:22])[O:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]2[N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[NH:7][CH:9]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 27786912-Bromo-1-[4-(trifluoromethoxy)phenyl]ethan-1-oneHCID 178475102HCID 178475102, compound

Product 1

HCID 178474425N-[4-(4-Trifluoromethoxy-phenyl)-1H-imidazol-2-yl]-acetamideYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acetyl guanidine (2.6 g, 25.7 mmol, 3.0 eq) was dissolved in anhydrous DMF (40 mL) and 2-bromo-1-(4-trifluoromethoxy-phenyl)-ethanone (2.4 g, 8.6 mmol, 1.0 eq) was added; the mixture was stirred at room temperature for 4 days. DMF was removed under reduced pressure, the residue was washed with water, filtered and dried over sodium sulphate; after crystallization from MeOH 0.7 g of the title compound were recovered (yield 30%).

Workup

  1. customDMF was removed under reduced pressure
  2. washthe residue was washed with water
  3. filtrationfiltered
  4. dry with materialdried over sodium sulphate
  5. customafter crystallization from MeOH 0.7 g of the title compound
  6. customwere recovered (yield 30%)

Sources & evidence

ORD record
ord-ddeb8889fef54d17a5eafa85ec0c862d
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

Loading…