N-bromobutanimide → Diethyl 2-bromo-1H-imidazole-4,5-dicarboxylate

HRID 1446042Notes

Reaction equation

HRID 1446042 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH:9]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:11]=[CH:10]1>C(#N)C>[Br:1][C:10]1[NH:9][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 350670Diethyl 1H-imidazole-4,5-dicarboxylate

Product 1

HCID 14752650Diethyl 2-bromo-1H-imidazole-4,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under an argon atmosphere 3.30 g (18.54 mmol) N-bromosuccinimide were added to a solution of 2.60 g (12.25 mmol) diethyl imidazole-4,5-dicarboxylate in 30 ml acetonitrile. The solution was stirred for 24 hours in the dark at ambient temperature and then evaporated down. The residue was taken up in 150 ml of ethyl acetate and washed twice each with saturated aqueous sodium chloride solution and saturated aqueous sodium thiosulphate and once with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate and the solvent was removed.

Workup

  1. customevaporated down
  2. washwashed twice each with saturated aqueous sodium chloride solution and saturated aqueous sodium thiosulphate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-cb64f0ba23d94bd7b340c3ab9aeb92d6
Source dataset
uspto-grants-2010_02
Patent number
US07667035B2

Reaction notes

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