Reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[CH2:11]([O:13][C:14](=[O:22])[CH:15]([C:19](=O)[CH3:20])[C:16](=O)[CH3:17])[CH3:12].C(Cl)(Cl)Cl>C(O)C.N1C=CC=CC=1>[CH2:11]([O:13][C:14]([C:15]1[C:16]([CH3:17])=[N:10][N:9]([C:6]2[CH:7]=[CH:8][C:3]([Br:2])=[CH:4][CH:5]=2)[C:19]=1[CH3:20])=[O:22])[CH3:12]Participants
Procedure
p-Bromophenylhydrazine hydrochloride (10 mmol, 2.5 g) was added to 2-acetyl-3-oxo-butyric acid ethyl ester (10 mmol, 1.7 g) in ethanol (10 mL) and pyridine (10 mL). The mixture was stirred overnight at room temperature. Thin layer chromatographic (TLC) analysis using chloroform indicated the reaction was complete. The solvents were removed under vacuum. The residue was dissolved in 150 mL ether, then washed with 50 mL water to remove the pyridine. The ether, was dried over sodium sulfate (NaSO4), the solids filtered, then the solvents were removed under vacuum. The resulting oil was purified on a silica column. The named product crystallized upon standing in the column effluent, m.p. 71° C.-73° C. Analysis by 1H-NMR and 13C-NMR verified synthesis the named product.
Workup
- customThe solvents were removed under vacuum
- dissolutionThe residue was dissolved in 150 mL ether
- washwashed with 50 mL water
- customto remove the pyridine
- dry with materialThe ether, was dried over sodium sulfate (NaSO4)
- filtrationthe solids filtered
- customthe solvents were removed under vacuum
- customThe resulting oil was purified on a silica column
- customThe named product crystallized
- customsynthesis the named product
Sources & evidence
- ORD record
- ord-30d3f3a88c1e42c4aade5cd7833313fb
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06569885B1
Linked notes
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