N-bromobutanimide → HCID 66868795, compound

HRID 729995

Reaction equation

HRID 729995 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH3:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[CH2:9]([N:16]1[C:20]([Br:1])=[CH:19][N:18]=[C:17]1[CH3:21])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 836991H-Imidazole, 2-methyl-1-(phenylmethyl)-

Product 1

HCID 66868795HCID 66868795, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Add N-bromosuccinimide (7.85 g, 44 mmol) to a solution of 1-benzyl-2-methyl-1H-imidazole (8.0 g, 46 mmol) in chloroform (200 mL) and stir for 6 h. Wash with saturated aqueous sodium hydrogen carbonate and saturated aqueous NaCl, dry over MgSO4, and filter through a pad of silica gel. Concentrate filtrate and suspend the residue in diethyl ether (600 mL), heat to reflux, and filter hot. Concentrate ether filtrate to give the title compound as a tan solid (9.3 g).

Workup

  1. washWash with saturated aqueous sodium hydrogen carbonate and saturated aqueous NaCl
  2. dry with materialdry over MgSO4
  3. filtrationfilter through a pad of silica gel
  4. temperatureheat
  5. temperatureto reflux
  6. filtrationfilter hot

Sources & evidence

ORD record
ord-42c98c3babcb49f8bfa577afcb1884f8
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Linked notes

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