Acetophenone → Phenacyl bromide

HRID 877010Notes

Reaction equation

HRID 877010 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:10]Br>C(O)(=O)C>[CH2:2]([Br:10])[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 24408Bromine

Product 1

HCID 6259Phenacyl bromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Synthesis of 2-amino-4-arylimidazolamine of the formula (48) (wherein R4, R5, R6, R7 R8 and R9 are as defined above) is described in Scheme 9. Thus, reaction of acetophenone derivative of formula (45) with bromine in acetic acid gives phenacyl bromide, which on reaction with acetyl guanidine in acetonitrile at reflux temperature gives N-acetyl imidazole of the formula (47). The N-deacetylation of (47) under acidic conditions affords 2-amino-4-arylimidazoles of the formula (48). This is similar to the procedure reported by Thomas, L. et al in J. Org. Chem., 1994, 59, 7299-7305.

Sources & evidence

ORD record
ord-d4c12c3bc1bc40b880395d771cb47b98
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

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