Imidazole → HCID 67662805, compound
Reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O.[CH2:19]([NH:24][C:25](=[O:37])[CH2:26][C:27]1[CH:32]=[C:31](Br)[CH:30]=[C:29]2[O:34][CH2:35][O:36][C:28]=12)[CH2:20][CH2:21][CH2:22][CH3:23]>C(OCC)(=O)C>[CH2:19]([NH:24][C:25](=[O:37])[CH2:26][C:27]1[CH:32]=[C:31]([C:2]2[NH:1][CH:5]=[CH:4][N:3]=2)[CH:30]=[C:29]2[O:34][CH2:35][O:36][C:28]=12)[CH2:20][CH2:21][CH2:22][CH3:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
Imidazole (1.11 g, 16.3 mmol), potassium carbonate (2.78 g, 20.1 mmol), cuprous chloride (0.31 g, 3.1 mmol), and N-methylpyrrolidone (25 ml) were added to N-pentyl-(5-bromo-2,3-methylenedioxyphenyl)acetamide (4.65 g, 14.8 mmol), and the mixture was stirred at 200° C. for 10 hours. The reaction mixture was cooled and added with ethyl acetate (30 ml) and the precipitates were removed by filtration. The ethyl acetate layer was successively washed with 10% aqueous ammonia and with saturated brine, and dried over anhydrous sodium sulfate, and then the solvent was evaporated. The residue was purified by silica gel chromatography (Wako Gell C-300: 100 g, eluent: methanol/chloroform=1/50-1/20) to give N-pentyl-(5-imidazolyl-2,3-methylenedioxyphenyl)acetamide (2.13 g) as an oil.
Workup
- temperatureThe reaction mixture was cooled
- customthe precipitates were removed by filtration
- washThe ethyl acetate layer was successively washed with 10% aqueous ammonia and with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated
- customThe residue was purified by silica gel chromatography (Wako Gell C-300: 100 g, eluent: methanol/chloroform=1/50-1/20)
Sources & evidence
- ORD record
- ord-cc388431566648aaab318c3159f27fc7
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05807860
Reaction notes
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