Thiobarbital

Thiobarbital is a drug which is a barbiturate derivative. It is the thiobarbiturate analogue of barbital.

Thiobarbital
Identifiers
IUPAC name
  • 5,5-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.000.929
Chemical and physical data
FormulaC8H12N2O2S
Molar mass200.259 g·mol−1
3D model (JSmol)
SMILES
  • O=C1NC(=S)NC(=O)C1(CC)CC
InChI
  • InChI=1S/C8H12N2O2S/c1-3-8(4-2)5(11)9-7(13)10-6(8)12/h3-4H2,1-2H3,(H2,9,10,11,12,13) Y
  • Key:QGVNJRROSLYGKF-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Synthesis
Thiobarbital synthesis:[1][2]

It is of note that although the drug can be prepared by the above route (cf e.g. thialbarbital), reaction of barbital with phosphorus pentasulfide constitutes an alternative route to thiobarbital.

References
  1. Fischer E, Dilthey A (1904). "Ueber C-Dialkylbarbitursäuren und über die Ureïde der Dialkylessigsäuren". Justus Liebig's Annalen der Chemie. 335 (3): 334–368. doi:10.1002/jlac.19043350303.
  2. Carrington HC (1944). "45. The action of phosphorus pentasulphide on barbituric acids". Journal of the Chemical Society (Resumed): 124. doi:10.1039/JR9440000124.


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