1831. Carbromal

Nomenclature

CAS number: 77-65-6
N-(Aminocarbonyl)-2-bromo-2-ethylbutanamide; (α-bromo-α-ethylbutyryl)urea; (α-bromo-α-ethylbutyryl)carbamide; bromodiethylacetylurea; bromodiethylacetylcarbamide; Tildin; Adalin (Bayer); Planadalin; Diacid (Daro); Addisomnol (Synochem); Bromadal; Uradal; Nyctal.
C7H13BrN2O2; mol wt 237.09.
C 35.46%, H 5.53%, Br 33.70%, N 11.82%, O 13.50%.

Description and references

Prepd by heating urea (to ≈50°) with α-bromo-α-ethylbutyryl bromide (C2H5)2CBrCOBr, see DE 225710 (1910); Frdl. 10, 1160; Chem. Zentralbl. 1910, II, 1008. Patent literature: Slotta, Grundriss der modernen Arzneistoff-Synthese (Stuttgart, 1931); H. P. Kaufmann, Arzneimittel-Synthese (Berlin, 1953).

Chemical structure

Properties

Crystals, mp 116-119°. One gram dissolves in about 3000 ml water, 18 ml alcohol, 3 ml chloroform, 14 ml ether. Very sol in boiling alcohol; dissolves in concd sulfuric, nitric and hydrochloric acids, from which it is precipitated on dilution with water. Dissolved by solns of alkali hydroxides.

Therapeutic Category

Sedative, hypnotic.

Keywords

Sedative/Hypnotic; Acylic Ureides