N-Iodosuccinimide → 2-n-Butyl-5-hydroxymethyl-4-iodoimidazole
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
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 42.5 °C
Procedure
N-Iodosuccinimide (148.75 g, 0.661 mol) was added to a stirred solution of 2-n-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 L of water, and chilled. The crystalline product which formed was collected by filtration, washed with water, and dried to give 1.74.5 g (95%) of crystals; mp 166-166.5° C.
Workup
- temperaturechilled
- customThe crystalline product which formed
- filtrationwas collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-963353a592144156a5b116c9d881bf3b
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05929249
Reaction notes
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