Triethylamine → N-{2-[(2-methylacryloyl)amino]ethyl}-3-oxobutanamide
Reaction equation
Br.[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:11])[CH2:7][C:8]([CH3:10])=[O:9].C(N(CC)CC)C.[C:19](Cl)(=[O:23])[C:20]([CH3:22])=[CH2:21]>CN(C)C=O>[C:6]([NH:5][CH2:4][CH2:3][NH:2][C:19](=[O:23])[C:20]([CH3:22])=[CH2:21])(=[O:11])[CH2:7][C:8]([CH3:10])=[O:9]Participants
5
Conditions
- Temperature
- 20 °C
Procedure
Crude N-(2-aminoethyl)acetoacetamide hydrobromide (50 g, 0.18 mole) was dissolved in N,N-dimethylformamide (500 ml). Triethylamine (78 g, 0.4 mole) and methacryloyl chloride (19 g, 0.18 mole) were added simultaneously at 0° C. The reaction solution was then stirred at 0° C. for 1 hour and at 20° C. for 20 hours. The resulting solution was filtered, the solvent removed, and the residue dissolved in chloroform (500 ml). The solution was then washed with 10% hydrochloric acid (200 ml), then water (200 ml) and dried over anhydrous magnesium sulfate. The solvent was then removed. The residue was recrystallized from ethanol/ether (1:1). The resulting compound had a m.p. of 86°-90° C. The yield was 25%.
Workup
- filtrationThe resulting solution was filtered
- customthe solvent removed
- dissolutionthe residue dissolved in chloroform (500 ml)
- washThe solution was then washed with 10% hydrochloric acid (200 ml)
- dry with materialwater (200 ml) and dried over anhydrous magnesium sulfate
- customThe solvent was then removed
- customThe residue was recrystallized from ethanol/ether (1:1)
Sources & evidence
- ORD record
- ord-630bd8c0de794b12a04db9431f51d612
- Source dataset
- uspto-grants-1983_12
- Patent number
- US04421915
Reaction notes
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