Methanol → 1,3-Dihydro-1-methyl-3-[4-(5-methyl-1H-imidazol-1-yl)-2-butynyl]-2H-imidazol-2-one
Reaction equation
Br[CH2:2][C:3]#[C:4][CH2:5][N:6]1[CH:10]=[CH:9][N:8]([CH3:11])[C:7]1=[O:12].C([N:16]1[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]1)(=O)C.CO>C(#N)C>[CH3:11][N:8]1[CH:9]=[CH:10][N:6]([CH2:5][C:4]#[C:3][CH2:2][N:18]2[C:19]([CH3:21])=[CH:20][N:16]=[CH:17]2)[C:7]1=[O:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
A mixture of 1-(4-bromo-2-butynyl)-1,3-dihydro-3-methyl-2H-imidazol-2-one (4.12 g, 0.018 mol) and 1-acetyl-4-methylimidazole (4.47 g, 0.036 mol) in acetonitrile (6 mL) was heated in an oil bath (bath temperature 85° C.) for 1 hr. Methanol (20 mL) was added and, after 1 hr, the solvents were removed and the residue was partitioned between ethyl acetate and 4N NaOH solution. The ethyl acetate was removed and the residual oil was chromatographed on silica gel using methanol:chloroform as eluant to give 3.3 g of product.
Workup
- customthe solvents were removed
- customthe residue was partitioned between ethyl acetate and 4N NaOH solution
- customThe ethyl acetate was removed
- customthe residual oil was chromatographed on silica gel
Sources & evidence
- ORD record
- ord-c74af43ed87a4348b337c65338345d81
- Source dataset
- uspto-grants-1993_07
- Patent number
- US05225567
Reaction notes
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