Ethanol → 2-Butyl-4-chloro-5-(hydroxymethyl)imidazole

HRID 439599Notes

Reaction equation

HRID 439599 reaction equation
[Cl: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]([Cl:1])[N:17]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 31398ChlorosuccinimideHCID 15338146(2-butyl-1H-imidazole-4,5-diyl)dimethanol

Product 1

HCID 27356622-Butyl-4-chloro-5-(hydroxymethyl)imidazole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.45 Grams (10.9 mmol) of an N-chlorosuccinimide was added to a solution consisting of 1.91 g (10.4 mmol) of a 2-butyl-4,5-bis(hydroxymethyl) imidazole, 100 ml of ethanol and 40 ml of 1,4-dioxane maintained at room temperature. The mixture was reacted for 18 hours with stirring and, then, the solvent was distilled off under reduced pressure. The resulting reaction product was washed with water and was recrystallized from acetonitrile to obtain a pale yellowish scale-like crystalline 2-butyl-4- chloro-5-(hydroxymethyl) imidazole in an amount of 1.00 g (yield, 51%). Recrystallization was further effected with acetonitrile to obtain the milk-white crystalline compound in pure form.

Workup

  1. customThe mixture was reacted for 18 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe resulting reaction product
  4. washwas washed with water
  5. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-dd1d8daf44984c4598fbfebd982053f5
Source dataset
uspto-grants-1996_05
Patent number
US05514811

Reaction notes

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