Thiocyanate and Isothiourea Derivatives of Barbituric Acid - Journal of

GLENNS.SKINNER AND WILLIAM H. ~YALITZ,JR.

408

ing, the adduct solidified, and was recrystallized from 3060" petroleum-ether. The yield of material with the m.p. 75' was 235 mg. (86%). For analysis a sampleowas recrystallized from petroleum-ether, m.p. 75.0-75.6

.

[COSTRIBUTIOX FROM

THE

VOl. 74

Anal. Calcd. for ClfHZ201: C, 74.42; H, 8.08. C, 74.51; H, 8.31.

CAMBRIDGE, MASS.

Found:

RECEIVED JULY 9, 1951

CHEMISTRY DEPARTMENT, LiNIVERSITP

OF

DELAWARE ]

Thiocyanate and Isothiourea Derivatives of Barbituric Acid RY

s. SKINNER AND WILLIAM H. ~VAITZ, JR.

C>LENN

A series of thiocyanate and isothiourea derivatives of barbituric acid have been prepared and subjected to pharmacological testing. The thiocyanate resisted hydrolysis without cleavage of the ring. The isothiourea derivative was smoothly hydrolyzed to the mercaptobarbituric acid. None of the compounds gave hypnosis or anesthesia. The isothiouronium bromides showed some anticonvulsant activity.

In a previous report' we have described a series of 5-(0-xanthoethy1)- and 5-(fl-mercaptoethyl)-barbituric acids. The establishment of the carbonsulfur bond a t this position has now been extended to include the thiocyanates and isothiouronium salts (I).

r

0

c

K

;1"*

I

/' C

\\

H1T\-=C--S--CH2CH2

'

SEI I C=O I

C - AI1

I,

C)

L

1

1

Br-

Both the thiocyanates and the isothiouronium salts (Table I) were easily prepared in good yields by the action of potassium thiocyanate and thiourea, respectively, on the p-bromoethylbarbituric acid derivatives in alcohol. These reagents are advantageous since they are more stable than the xanthates. 'rABLE 1 BARBITURIC ACIDSRR'C( CONH),CO (R,, T\\'CSCH&H2-; Rz,(H&=C(NHe)SCH&H2-)'Br-; Rai HN=C(NHt)SCH2CH,-) I