Ethyl Acetate → 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(OCC)(=O)C>CN(C1C=CN=CC=1)C.O1CCOCC1.COCCO>[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
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
4-DMAP (1.2 g; 10 mmol) and N-iodosuccinimide (25 g; 111 mmol) were added to a solution of 2-butyl-4-hydroxymethyl-imidazole (15.4 g; 100 mmol) in dioxane (210 ml) and 2-methoxyethanol (140 ml) and the mixture was stirred overnight at 50° C. Concentration gave 44.4 g of a brownish-yellow magma (theory; 28 g), which was further reacted without further purification. For characterisation, 2 g of the crude product were dissolved using ethyl acetate and washed with 5% NaHCO3 solution and saturated sodium chloride solution. Drying and concentration of the organic phases gave 1.2 g of a yellow solid [97% of theory; m.p.: 135°-40° C. (dec.); Rf : 0.24 (methylene chloride:methanol=10:1)].
Workup
- concentrationConcentration
- customgave 44.4 g of a brownish-yellow magma (theory; 28 g), which
- customwas further reacted without further purification
- washwashed with 5% NaHCO3 solution and saturated sodium chloride solution
- customDrying
Sources & evidence
- ORD record
- ord-7ad7dd7e68044ab1a3b253011cd2d1e6
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05776964
Reaction notes
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