Phenacyl bromide → HCID 178474414, compound

HRID 1367836Notes

Reaction equation

HRID 1367836 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-b4bae55fc8414f109c534a56b0c32ed6
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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