4-Bromobenzoyl chloride → 4-bromo-N-[3-(1H-imidazol-1-yl)propyl]benzamide

HRID 23923

Reaction equation

HRID 23923 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[Br:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1>C(O)C>[Br:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH:1][CH2:2][CH2:3][CH2:4][N:5]2[CH:9]=[CH:8][N:7]=[CH:6]2)=[O:16])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 685154-Bromobenzoyl chlorideHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 34259134-bromo-N-[3-(1H-imidazol-1-yl)propyl]benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(3-Aminopropyl)imidazole (2.39 ml, 0.02 mol) was added to a solution of 4-bromobenzoyl chloride (4.0 g, 0.218 mol) in ethanol (250 ml). The mixture was stirred at ambient temperature for 18 hours. The volatiles were removed by evaporation and the residue was purified by chromatography eluting with hexane/dichloromethane (50:50) increasing in polarity to dichloromethane/methanol (80:20) to give the title compound. NMR: 1.95 (m, 2H), 3.20 (q, 2H), 4.0 (t, 2H), 6.87 (s, 1H), 7.19 (s, 1H), 7.64 (d, 2H), 7.68 (s, 1H), 7.78 (d, 2H), 8.58 (t, 1H); m/z: 308 [MH]+.

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue was purified by chromatography
  3. washeluting with hexane/dichloromethane (50:50)
  4. temperatureincreasing in polarity to dichloromethane/methanol (80:20)

Sources & evidence

ORD record
ord-1ccd850b8d5f4b728e33415745f93e9f
Source dataset
uspto-grants-2005_02
Patent number
US06855719B1

Linked notes

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