NEW COUPOVSDS
July 1966
643
T LBLE I SOME
HYDRAZOSES O F 5-PHETYL-2,4-THI.~ZOLIDINEDIONE O=C-NH C,H,-CH
{
I
C=NN=R
S '' LIP, O C
R
----%
Yield,
%
Formula
C O S ( CeH:)N( CH,)C( CHd)=CCH=
259-260
90.02
C21H1&jOrS
CON(CeH;)N(CHa)C(CHa)=CNHCH=
254
56.00
CH~CH?OCHICH~NCH=
275 250
L
i
calcd----
H
C
found--H
7 %
S
C
S
62.21 4 . 7 2 17.28 62 52 4.90
17.01
C Z I H ~ O S ~ O ~59.99 S 4.80
19 99 59.42 5 07
20.10
18.32
Ci4Hi6?ia01S
38.00 5.50
14.50 57.81 4.94
14.79
38.40
C17Hd40Sa
57.95 3.43 15.90 57.20 3.98
15.81
antianemia, and antithyroid a c t i o i ~ - ~Some 5,5-dialkyl derivatives possess hypnotic properties.7-10 The methods for the preparation of both the parent compoiindll and many of its 12-15 Four new analogs derivatives are described iii literat~ire.~-~~s are listed in Table I.
tent neiirotoxic and convulsive activity in a "bteroidlike" molecrile, ~e iuidertook the synthezib aiid phy4ological evaluation of the heterocyclic portion of the alkaloid. K e suspected it to be responsible for the iiricommon activity.'
Experimental Section16 4-Formylantipyrine Hydrazone of 5-Phenyl-2,4-thiazolidinedione.-4-Antipyrine carboxylate (4.0 g, 0.02 mole) was dissolved in ethanol and made basic with NaOH. Thiosemicarbazide (1.8 g, 0.02 mole) was then added. After allowing the mixture t o stand for 10 min ethyl phenylchloroacetate (4.0 g, 0.02 mole) was added aiid the mixt'ure was shaken. Sodium acetate (1.6 g, 0.02 mole) and 6.0 ml of dilute acetic acid were then added and the mixture was refluxed for 30 min. Upon cooling a yellow crystalline solid was filtered off, air dried, and recrystallized from ethanol The hydrazones of S-formylaminoantipyrine, K-formylmorpholine, and 9-formylbenzythiazole Kere prepared and purified in the same manner. _
_
~
(3) E. V. Vladeimirskaya, N . AI. Turkevich, Zh. Obshch. K h i m . , 26, 2150 (1955); Chem. Abstr., 60, 8605b (1956). (4) S . XI. Turkerich, E. V. Vladsimirskaya, Z h . Obshch. K h i m . , 24, 2010 (1954); Chem. Abstr., 49, 14737i (1955). (5) 3. M . Kapustyak, Farm. Zh., 14, No. 3, 6 (1959); Chem. Abstr., 66, 56501'(1961). (6) iV..\I. Turkevich, I
