Phenacyl bromide → HCID 178474414, compound

HRID 1910107Notes

Reaction equation

HRID 1910107 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[C:11]([NH:14][C:15]([NH2:17])=[NH:16])(=[O:13])[CH3:12]>CN(C=O)C.CCOC(C)=O>[C:5]1([C:3]2[N:16]=[C:15]([NH:14][C:11](=[O:13])[CH3:12])[NH:17][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 178475102HCID 178475102, compound

Product 1

HCID 178474414HCID 178474414, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.0 g (10 mmol) of 2-bromoacetophenone in DMF (30 mL) was added 3.0 g (29 mmol) 1-acetylguanidine in one portion, the reaction mixture was stirred at rt for 2 days. The reaction mixture was diluted with EtOAc (250 mL) and washed with saturated NH4Cl aq. solution (50 mL). The organic phase was dried over MgSO4 and concentrated under vacuum. The residue was purified by a flash column chromatography eluting with EtOAc to give N-(4-phenyl-1H-imidazol-2-yl)-acetamide. (0.5 g, 24%). LCMS: 203 (M+1)+.

Workup

  1. washwashed with saturated NH4Cl aq. solution (50 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by a flash column chromatography
  5. washeluting with EtOAc

Sources & evidence

ORD record
ord-6b06ec14e0e140d9baf33ad8f7edf21a
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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