Carbromal

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Carbromal
Skeletal formula of carbromal
Names
IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
Identifiers
77-65-6 YesY
ATC code N05CM04
ChEMBL ChEMBL1697828 YesY
ChemSpider 6243 YesY
EC number 201-046-6
Jmol-3D images Image
Image
KEGG D02619 YesY
MeSH carbromal
PubChem 6488
UNII 0Y299JY9V3 YesY
Properties
C7H13BrN2O2
Molar mass 237.10 g·mol−1
Appearance White crystals
Odor Odourless
log P 1.623
Acidity (pKa) 10.69
Basicity (pKb) 3.31
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).