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Encyclopedia Britannica



HYDANTOIN (glycolyl urea), C3H4N202

This article appears in Volume V14, Page 30 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: HOR-I25
HYDANTOIN (glycolyl urea), C3H4N202 or CO< NHCH2 NHCO
the ureide of glycollic acid, may be obtained by heating allantoin or alloxan with hydriodic acid, or by heating bromacetyl urea with alcoholic ammonia. It crystallizes in needles, melting at 216 C.
When hydrolysed with baryta water yields hydantoic
(glycoluric) acid,H2N CO .NH . CH2
CO2H
 , which is readily soluble in hot water, and on heating with hydriodic acid decomposes into ammonia, carbon dioxide and glycocoll, CH2NH2CO2H. Many substituted hydantoins are known; the a-alkyl hydantoins are formed on fusion of aldehyde- or ketone-cyanhydrins with urea, the '3-alkyl hydantoins from the fusion of mono-alkyl glycocolls with urea, and the 7-alkyl hydantoins from the action of alkalis and alkyl iodides on the a-compounds. y-Methyl hydantoin has been obtained as a splitting product of caffeine (E. Fischer, Ann., 1882, 215, p. 253).


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