Methacrylamide → Ethyl (2-methylacryloyl)carbamate
Reaction equation
[C:1]([NH2:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].CC(C)([O-])C.[K+].Cl[C:14]([O:16][CH2:17][CH3:18])=[O:15]>O1CCOCC1>[C:1]([NH:6][C:14](=[O:15])[O:16][CH2:17][CH3:18])(=[O:5])[C:2]([CH3:4])=[CH2:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
In 200 g of dioxane, 4.26 g of methacrylamide and 6.37 g of potassium t-butoxide were dissolved and the solution was stirred for 60 minutes at 60° C. Then, 5.43 g of ethyl chloroformate was dissolved in 50 g of dioxane and the solution was added dropwise to the reaction mixture in 2 hours. After removing tetrahydrofurane in vacuo, 1000 g of water was added to the residue and the solution was extracted with 500 ml of ethyl acetate. The extract was evaporated in vacuo. The crude product was subjected to column chromatography, thereby obtaining 1.0 g of ethyl N-methacryloylcarbamate. Melting point of the product was 73°-74° C.
Workup
- additionthe solution was added dropwise to the reaction mixture in 2 hours
- customAfter removing tetrahydrofurane in vacuo, 1000 g of water
- additionwas added to the residue
- extractionthe solution was extracted with 500 ml of ethyl acetate
- customThe extract was evaporated in vacuo
Sources & evidence
- ORD record
- ord-83c145ec92ec48e7946d84781a40aa63
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05187306
Reaction notes
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