Dec., 1942
5,5-DIMETHYLHYDANTOINSCONTAINING A -NRR' [CONTRIBUTION FROM THE
2881
SUBSTITUENT
DEPARTMENT OF CHEMISTRY, THEUNIVWSITY
OF TEXAS]
5,5-Dimethylhydantoins Containing a -NRR' Substituent. I1 BY HENRYR. HENZEAND DAVIDD. HUMPHREYS'J About four years ago there was reporteda from verted into substituted hydantoins by the Buchthis Laboratory the synthesis of a series of 5,5- erer6 procedure. In general, 0.1 mole of the Ndimethylhydantoins containing a dialkylamino alkyl-n-butylaminoacetone was dissolved in 75 substituent in which the two alkyls were alike. cc. of ethyl alcohol; then a solution of 0.11 mole More recently,4 was recorded the preparation of of potassium cyanide dissolved in 60 cc. of water another series of 5,5-&methylhydantoins, these, was added. Ammonium carbonate (0.3 mole) was however, containing a -NRR' substituent in crushed to a coarse powder and added to the which R represented a normal alkyl group or ketone-cyanide mixture. Now, 60% alcohol phenyl and R' phenyl or benzyl. Intermediate solution was added until only one liquid phase the between these two series would be that containing existed in the reaction mixture a t 55-60'; a -NRR' substituent in which R and R' repre- ammonium carbonate was completely in solution after a few hours. The warming continued a t sent different alkyl groups. As a result of another investigation6 there were 55-60' under a reflux condenser for ten to twelve available eight N-alkyl-n-butylaminoacetones. hours. The light yellow solution was chilled Each of these has been converted into the corre- causing virtually complete separation of the sponding hydantoin derivative by reaction with hydantoin. . The latter was recrystallized from ammonium carbonate and potassium cyanide. diluted alcohol; in some instances addition of Through the courtesy of Parke, Davis and Com- petroleum ether to a benzene solution of the hypany, six of these hydantoins have received pre- dantoin proved to be an efficacious method for liminary testing on mice intraperitoneally for purification. Data concerning certain physical toxicity and possible hypnotic action. The properties for and analyses of the eight hydanN-methyl and N-ethyl members of the series toins have been placed in Table I. TABLE I
HN-CO
I
OC
I
R
5-[N-ALKYL-?t-BUTYLAaarNOMETHYL]-5-METHYLHYDANTOINS Hi$-C-cH&
