N-Iodosuccinimide → 2-n-Butyl-5-hydroxymethyl-4-iodoimidazole

HRID 37003

Reaction equation

HRID 37003 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([C:13]1[NH:14][CH:15]=[C:16]([CH2:18][OH:19])[N:17]=1)[CH2:10][CH2:11][CH3:12]>C(O)C.O>[CH2:9]([C:13]1[NH:17][C:16]([CH2:18][OH:19])=[C:15]([I:1])[N:14]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 178418407HCID 178418407, compound

Product 1

HCID 148985472-n-Butyl-5-hydroxymethyl-4-iodoimidazoleYield 95.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-Iodosuccinimide (148.75 g, 0.661 mol) was added to a stirred solution of 2-butyl-4-hydroxymethylimidazole (100.78 g, 0.652 mol) in 500 mL of absolute ethanol. After 20 minutes the solution was heated to 40°-45° C. for 45 minutes, diluted with 2.5 liters of water, and chilled. The crystalline product was collected by filtration, washed with water, and dried to give 174.5 g (95%) of crystals; mp 166°-166.5° C.

Workup

  1. temperatureAfter 20 minutes the solution was heated to 40°-45° C. for 45 minutes
  2. temperaturechilled
  3. filtrationThe crystalline product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-dba550157d9b489c8894daa59a6bd08b
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Linked notes

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