~.
1 lie residue from the distillation was recrystallized four Kerishaw, Ilreisbach, Ziff u l d Grcen10in 100 i d . of absolute times from aqueous ethanol to give 430 mg. of the starting ethanol, 2.0 g. of \V-6 Raney nickel catalyst'* was added and quinazolone (m.p. 159-160.5') a n t 350 mg. of 3-phenyl-4the resulting mixture was heated under reflux for 90 minutes. (3H)quinazolone, m.p. 142-142.5 , reportedI6 139". T h e catalyst powder was removed by filtration and the Control Experiment.-To a solution of 0.90 g. of I-K,N- filtrate was distilled through a short-path still. ;1 satudimethylaminopropanel7 in 100 ml. of absolute ethanol, 2.0 rated solution of picric acid in 95% ethanol was added to the g. of W-6 Raney nickel ~ a t a l y s t was ' ~ added and the resultfirst 50-rnl. fraction of the distillate until the solution was ing mixture was heated under reflux for 90 minutes. neutral t o moist litmus. Concentration of this solution Djmethyl-n-propylammonium picrate, 480 mg., m.p. 111-112 , gave 270 mg. of dimethylisopropylammonium picrate, m . p . reported18 108-109°, was isolated by the procedure described 242-243" dec., reportedlj 240-241" dec. above. authors gratefully acDesulfurization of 2-N,N-Dimethylamino-l-propylthi- Acknowledgment. -The uronium Chloride Hydrochloride.-To a solution of 1.O g. knowledge the generous financial support of the of 2-N,N-dimethylamino-l-propylthiuroniumchloride hy- Smith, Kline and French Laboratories, Philadelphia, drochloride (m.p. 202-204') prepared by the method of
Penna.
(16) C. Paal a n d M. Busch, Rer., 22, 2683 (1889). (17) See L. W a l t e r a n d J. A . Pappalardo, J. Org. Chctiz., 22, 840 (1957). (18) W. H a n h a r t a n d C. K. Ingold, J . Chem. Soc., 907 (1'337).
[CONTRIBUTION FROM T H E
(19) This c
