N-bromobutanimide → HCID 54267854, compound

HRID 439608Notes

Reaction equation

HRID 439608 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([C:16]1[NH:17][C:18]([CH2:23][OH:24])=[C:19](CO)[N:20]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.COC(O)C>O1CCOCC1>[CH2:9]([C:16]1[NH:17][C:18]([CH2:23][OH:24])=[C:19]([Br:1])[N:20]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 30156371-MethoxyethanolHCID 54135444HCID 54135444, compound

Product 1

HCID 54267854HCID 54267854, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.56 Grams (20 mmol) of the N-bromosuccinimide was added to a solution consisting of 4.86 g (20 mmol) of the 2-benzyl-4,5-bis(hydroxymethyl) imidazole, 80 mol of methoxyethanol and 30 ml of dioxane maintained at a temperature of 45° to 50° C. with stirring. The mixture was further reacted at the same temperature for 24 hours with stirring and, then, the solvent was distilled off under reduced pressure. The obtained reaction product was washed with water and was recrystallized from acetonitrile to obtain a 2-benzyl-4-bromo-5-(hydroxymethyl) imidazole in an amount of 2.1 g (yield, 39%).

Workup

  1. temperaturemaintained at a temperature of 45° to 50° C.
  2. customThe mixture was further reacted at the same temperature for 24 hours
  3. stirringwith stirring
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained reaction product
  6. washwas washed with water
  7. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d12987da2140480fb1419358b7519250
Source dataset
uspto-grants-1996_05
Patent number
US05514811

Reaction notes

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