Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Cl.Cl[CH2:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][CH:20]=1.C(OCC)C>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:14][CH2:15][C:16]2[N:17]=[CH:18][NH:19][CH:20]=2)=[CH:7][CH:6]=1Participants
Procedure
240 mg (60% in oil, 6 mmol) of sodium hydride are slowly added to a solution of 1.48 g (12 mmol) of 4-methoxyphenol in 7 ml of dimethylformamide and the mixture is stirred at room temperature for 1 hour. 200 mg (1.2 mmol) of 4-(2-chloroethyl)-1H-imidazole hydrochloride and tetrabutylammonium iodide (catalyst) are added and the mixture is stirred at 80° C. for 2 days. The reaction mixture is cooled and 150 ml of diethyl ether are added. The precipitate is separated by filtration and the filtrate is evaporated under reduced pressure to give a residue which is purified by preparative high performance chromatography. The title compound is converted to the oxalate and recrystallized from ethanol, M.p.: 178°-181° C. Elemental analysis: calculated: C 55.8 H 5.37 N 9.5 found: C 55.9 H 5.40 N 9.6
Workup
- stirringthe mixture is stirred at 80° C. for 2 days
- temperatureThe reaction mixture is cooled
- customThe precipitate is separated by filtration
- customthe filtrate is evaporated under reduced pressure
- customto give a residue which
- customis purified by preparative high performance chromatography
- customrecrystallized from ethanol, M.p.: 178°-181° C
Sources & evidence
- ORD record
- ord-1babf3b039d6463eb6daf9fc2869db28
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05708171
Linked notes
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