Potassium Carbonate → Ethyl 3-[1-(4-acetyl-2-nitrophenyl)-1H-imidazol-2-yl]-propanoate
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH:14]1[CH:18]=[CH:17][N:16]=[C:15]1[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>C(OCC)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([N:14]2[CH:18]=[CH:17][N:16]=[C:15]2[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)(=[O:10])[CH3:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 4′-fluoro-3′-nitroacetophenone 2.04 g, ethyl 3-(1H-imidazol-2-yl)propanoate 1.87 g, potassium carbonate 3.07 g and N,N-dimethylacetamide 28 mL was heated at 100° C. for 16.5 hours. The reaction liquid was allowed to cool off and to which 60 mL of diethyl ether was added, followed by filtration. Adding 100 mL of water to the filtrate, the organic layer was separated. The aqueous layer was extracted with 100 mL of diethyl ether. The extract was combined with the organic layer, washed twice with 20 mL of water and once with 10 mL of saturated brine by the order stated, and dried over magnesium sulfate. Distilling the solvent off under reduced pressure, 2.54 g of the title compound was obtained.
Workup
- customThe reaction liquid
- additionwas added
- filtrationfollowed by filtration
- additionAdding 100 mL of water to the filtrate
- customthe organic layer was separated
- extractionThe aqueous layer was extracted with 100 mL of diethyl ether
- washwashed twice with 20 mL of water and once with 10 mL of saturated brine by the order
- dry with materialdried over magnesium sulfate
- distillationDistilling the solvent off under reduced pressure
Sources & evidence
- ORD record
- ord-ea2bb06ad205429c9fe2058a25e3a81e
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299080B2
Reaction notes
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