Abstract
The difference between bromovalerylurea and bromodiethylacetylurea in their reaction with alkaline solutions was investigated. 5-Isopropylhydantoin and 2-ethyl-cis-crotonylurea were easily obtained, respectively, from bromovalerylurea and bromodiethylacetylurea when refluxed with ammonium hydroxide. On the other hand, α, β-unsaturated ureides were produced from both ureides when refluxed with basic organic solvents. Bromine-substituted morpholine or piperidine was also produced as a by-product and detected by mass spectrometry. Bromodiethylacetylurea in a considerably concentrated aqueous solution converted into 2-ethyl-trans-crotonylurea, although the cis form was the main product in a diluted solution. Bromovalerylurea was scarcely changed by refluxing in water. Formation of a geometrical isomer was based on the cis-trans transition which should be caused by hydrobromic acid derived from the hydrolysis of bromodiethylacetylurea. The rate of the transition depended on the concentration of the acid and the reaction time.
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