Benzoyl Peroxide → Diethyl 1-benzyl-2-(1-bromoethyl)imidazole-4,5-dicarboxylate

HRID 53055Notes

Reaction equation

HRID 53055 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH2:27]([N:34]1[C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[C:37]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[N:36]=[C:35]1[CH2:49][CH3:50])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N1C(C(OCC)=O)=C(C(OCC)=O)N=C1CBr)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:27]([N:34]1[C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[C:37]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[N:36]=[C:35]1[CH:49]([Br:1])[CH3:50])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 19036091Diethyl 1-benzyl-2-bromomethylimidazole-4,5-dicarboxylateHCID 19036266HCID 19036266, compound

Product 1

HCID 19036075Diethyl 1-benzyl-2-(1-bromoethyl)imidazole-4,5-dicarboxylateYield 97.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3.08 g of N-bromosuccinimide and 0.51 g of benzoyl peroxide were added to a solution of 5.19 g of diethyl 1-benzyl-2-ethylimidazole-4,5-dicarboxylate [prepared as described in step (i) above] in 100 ml of carbon tetrachloride, and the resulting mixture was heated under reflux for 1 hour. Following a procedure similar to that described in Preparation 42(ii), 6.29 g of the title compound were obtained as a syrup from the resulting reaction solution.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 hour

Sources & evidence

ORD record
ord-81cdc3cc35044c10a21d60c257b0c4e7
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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