Acetic Acid → 1,3-Diethyl 2-[(2-cyanoeth-1-EN-1-YL)amino]propanedioate
Reaction equation
O1[CH:5]=[CH:4][CH:3]=[N:2]1.C(O)(=O)C.C([O-])(=O)C.[Na+].Cl.[NH2:16][CH:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)C.C([O-])C.[Na+]>[C:3]([CH:4]=[CH:5][NH:16][CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Into a 500-mL round-bottom flask was placed isoxazole (25 g, 354.76 mmol, 1.00 equiv, 98%) in ethanol (100 mL) and sodium ethanolate (124 mL, 21%). The resulting solution was stirred at 0° C. for 30 min. Then acetic acid (6.9 mL, 98%), sodium acetate (20.5 g, 244.91 mmol, 0.69 equiv, 98%) and diethyl 2-aminomalonate hydrochloride (48 g, 222.26 mmol, 0.63 equiv, 98%) were added. The resulting solution was allowed to react, with stirring, for an additional 48 h at room temperature, concentrated under vacuum, dissolved in 200 mL of dichloromethane, washed with 2×100 mL of water, dried over anhydrous sodium sulfate and concentrated to afford 30 g (37%) of diethyl 2-(2-cyanovinylamino)malonate as a yellow oil
Workup
- customInto a 500-mL round-bottom flask was placed
- customto react
- stirringwith stirring, for an additional 48 h at room temperature
- concentrationconcentrated under vacuum
- dissolutiondissolved in 200 mL of dichloromethane
- washwashed with 2×100 mL of water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ca540acffaac4f938937ad79b72f3803
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653089B2
Reaction notes
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