Ethanolamine → 5-(3-Cyclohexene-1-yl)methylenehydantoin
Reaction equation
O.[NH:2]1[CH2:8][C:6](=[O:7])[NH:5][C:3]1=[O:4].[CH:9]1([CH:15]=O)[CH2:14][CH2:13][CH:12]=[CH:11][CH2:10]1.C(CN)O>C(O)(C)C>[CH:9]1([CH:15]=[C:8]2[NH:2][C:3](=[O:4])[NH:5][C:6]2=[O:7])[CH2:14][CH2:13][CH:12]=[CH:11][CH2:10]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
Fifty milliliters of water, 20 ml of isopropyl alcohol, 20.00 g of hydantoin, 24.22 g of 3-cyclohexene-1-carbaldehyde and 6.10 g of monoethanolamine were placed in a reactor equipped with a mechanical stirrer and a reflux condenser, the mixture was stirred in an oil bath at 120° C. while refluxing. After 3 hours of continued heating and stirring, the solution was cooled to 10° C., and the precipitated crystals were collected by filtration. These were suspended in 100 ml of a mixed solution of water and isopropyl alcohol (volumetric ratio=2:5), after which the crystals were again collected by filtration and dried under reduced pressure at 40° C. overnight, to obtain 33.45 g of 5-(3-cyclohexene-1-yl)methylenehydantoin. The yield was 87.0%. The crude crystals were recrystallized from ethanol to obtain a pure product.
Workup
- customequipped with a mechanical stirrer and a reflux condenser
- temperaturewhile refluxing
- temperatureAfter 3 hours of continued heating
- stirringstirring
- temperaturethe solution was cooled to 10° C.
- filtrationthe precipitated crystals were collected by filtration
- filtrationafter which the crystals were again collected by filtration
- customdried under reduced pressure at 40° C. overnight
Sources & evidence
- ORD record
- ord-41a58803c41f4d5ea2e3db49d95fb8ad
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05565575
Reaction notes
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