Carbromal

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Carbromal
Skeletal formula of carbromal
Names
IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.000.952
EC Number 201-046-6
KEGG
MeSH carbromal
UNII
Properties
C7H13BrN2O2
Molar mass 237.10 g·mol−1
Appearance White crystals
Odor Odourless
Density 1.544 g/cm3
Melting point 119 °C (246 °F; 392 K)
Soluble
Solubility soluble in chloroform, ether, acetone, benzene
log P 1.623
Acidity (pKa) 10.69
Basicity (pKb) 3.31
Structure
rhombic
Pharmacology
N05CM04 (WHO)
Related compounds
Related ureas
Bromisoval
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Carbromal is a hypnotic/sedative originally synthesized in 1909 by Bayer.[1]

Synthesis[edit]

Carbromal synthesis: DE 225710  (1910);[2][3] Patent literature:[4][5]

Diethylmalonic acid is decarboxylated to 2-ethylvaleric acid then converted via a Hell-Volhard-Zelinsky reaction to α-bromo-α-ethylbutyryl bromide. Reaction with urea with affords carbromal (4).

See also[edit]

References[edit]

  1. ^ DE 225710 
  2. ^ Frdl. 10, 1160
  3. ^ Chem. Zentralbl. 1910, II, 1008.
  4. ^ Slotta, Grundriss der modernen Arzneistoff-Synthese (Stuttgart, 1931)
  5. ^ H. P. Kaufmann, Arzneimittel-Synthese (Berlin, 1953).