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

HRID 1792767Notes

Reaction equation

HRID 1792767 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, 0.018 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-ec2c00ed3ca848f29957ef69ffc7e561
Source dataset
uspto-grants-2006_07
Patent number
US07078410B2

Reaction notes

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