N,N'-Dimethylethylenediamine → 1-Methyl-3-(1-methyl-1h-pyrazol-3-yl)-2-imidazolidinone
Reaction equation
I[C:2]1[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=1.[CH3:8][N:9]1[CH2:13][CH2:12][NH:11][C:10]1=[O:14].CNCCNC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COC1CCCC1.C(OCC)(=O)C.[Cu]I>[CH3:8][N:9]1[CH2:13][CH2:12][N:11]([C:2]2[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=2)[C:10]1=[O:14]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of 3-iodo-1-methyl-1H-pyrazole (250 mg), 1-methylimidazolidin-2-one (120 mg), copper(I) iodide (46 mg), N1,N2-dimethylethane-1,2-diamine (0.052 mL) and tripotassium phosphate (510 mg) in cyclopentyl methyl ether (5 mL) was stirred overnight at 120° C. The reaction mixture was diluted with ethyl acetate, and the mixture was washed successively with saturated aqueous ammonium chloride solution, water and saturated brine. The extract was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (161 mg).
Workup
- washthe mixture was washed successively with saturated aqueous ammonium chloride solution, water and saturated brine
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-42e3fc4414c2449da3e3d6902beb9e6c
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321757B2
Reaction notes
Loading…