Ethanol → 5-bromo-2-butyl-1H-imidazole-4-methanol

HRID 439607Notes

Reaction equation

HRID 439607 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([C:13]1[NH:14][C:15]([CH2:20][OH:21])=[C:16](CO)[N:17]=1)[CH2:10][CH2:11][CH3:12].C(O)C>O1CCOCC1>[CH2:9]([C:13]1[NH:14][C:15]([CH2:20][OH:21])=[C:16]([Br:1])[N:17]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 67184N-bromobutanimideHCID 15338146(2-butyl-1H-imidazole-4,5-diyl)dimethanol

Product 1

HCID 99915715-bromo-2-butyl-1H-imidazole-4-methanol

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 3.68 g (20.0 mmol) of the 2-butyl-4,5-bis(hydroxymethyl) imidazole, 40 ml of ethanol and 15 ml of dioxane maintained at a temperature of 45° to 50° C. with stirring. The mixture was further reacted at the same temperature for 30 minutes 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 pale yellowish scale-like crystalline 2-butyl-4-bromo-5-(hydroxymethyl) imidazole in an amount of 2.36 g (yield, 51%).

Workup

  1. temperaturemaintained at a temperature of 45° to 50° C.
  2. customThe mixture was further reacted at the same temperature for 30 minutes
  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-025b73636d7a460a9c2331cb9ff512a5
Source dataset
uspto-grants-1996_05
Patent number
US05514811

Reaction notes

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