2384. Clomethiazole

Nomenclature

CAS number: 533-45-9
5-(2-Chloroethyl)-4-methylthiazole; 4-methyl-5-(β-chloroethyl)thiazole; chlorethiazol; chlormethiazole; S.C.T.Z..
C6H8ClNS; mol wt 161.65.
C 44.58%, H 4.99%, Cl 21.93%, N 8.66%, S 19.84%.

Description and references

Prepd by condensation of thioformamide with chloroacetopropyl alcohol: Buchman, J. Am. Chem. Soc. 58, 1803 (1936); by chlorination of 4-methyl-5-(β-ethoxyethyl)thiazole: Clarke, Gurin, ibid. 57, 1876 (1935); by treating 5-(2-hydroxyethyl)-4-methylthiazole with thionyl chloride: Sawa, Ishida, J. Pharm. Soc. Jpn. 76, 337 (1956); by H2O2 oxidation of 2-mercapto-4-methyl-5-(β-chloroethyl)thiazole: CH 200248 (1938 to Hoffmann-La Roche). Prepn of methane and ethanedisulfonate: Charonnat et al., US 3031457 (1962).

Chemical structure

Properties

Oily, viscous liquid. d425 1.233. Characteristic disagreeable odor of thiazole compds. bp7 92°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 6001-74-7
C6H8ClNS.HCl; mol wt 198.11.
C 36.38%, H 4.58%, Cl 35.79%, N 7.07%, S 16.19%.

Properties

Crystals from abs ethanol + ether, mp 130°. Sol in water, alcohol.

Derivative

Methanedisulfonate.
C13H20Cl2N2O6S4; mol wt 499.47.
C 31.26%, H 4.04%, Cl 14.20%, N 5.61%, O 19.22%, S 25.68%.

Properties

Crystals from methanol + ether, mp 120°.

Derivative

Ethanedisulfonate.

Nomenclature

CAS number: 1867-58-9
Distraneurin (AstraZeneca); Hemineurin (AstraZeneca); Heminevrin (AstraZeneca).
C14H22Cl2N2O6S4; mol wt 513.50.
C 32.75%, H 4.32%, Cl 13.81%, N 5.46%, O 18.69%, S 24.98%.

Properties

Crystals from methanol + ether, mp 124°.

Use

Intermediate in some processes of vitamin B1 manufacture.

Therapeutic Category

Sedative, hypnotic, anticonvulsant.

Keywords

Anticonvulsant; Sedative/Hypnotic