80-77-3

Name	Chlormezanone
CAS	80-77-3
EINECS(EC#)	201-307-4
Molecular Formula	C11H12ClNO3S
MDL Number	MFCD00143951
Molecular Weight	273.74
MOL File	80-77-3.mol

Chemical Properties

Melting point	114 °C
Boiling point	534.5±50.0 °C(Predicted)
density	1.2205 (rough estimate)
refractive index	1.6300 (estimate)
storage temp.	Store at RT
solubility	Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form	Solid
pka	-2.37±0.40(Predicted)
color	White to Pale Yellow
Merck	14,2106
NIST Chemistry Reference	Chlormezanone(80-77-3)

Safety Data

RTECS	XJ1050000
HS Code	2934.99.4400
Hazardous Substances Data	80-77-3(Hazardous Substances Data)

Raw materials And Preparation Products

Hazard Information

Uses

Skeletal muscle relaxant

Definition

ChEBI: A 1,3-thiazine that is 1,3-thiazinan-4-one S,S-dioxide in which a hydrogen at position 2 is substituted by a 4-chlorophenyl group and the hydrogen attached to the nitrogen is substituted by methyl. A non-benzodiazepine muscle relaxant, it was used in the management of anxiety and in the treatment of muscle spasms until being discontinued worldwide by its manufacturer in 1996, due to rare but serious cutaneous reactions.

Biological Activity

Anxiolytic and skeletal muscle relaxant that acts at the benzodiazepine site of GABA A receptors.

Originator

Trancopal,Winthrop-Breon,US,1958

Manufacturing Process

A solution of 4-chlorobenzaldehyde is reacted with beta-mercaptopropionic acid and with methylamine. The mixture is refluxed in benzene and water is removed from an overhead separator. The reaction mixture was cooled, washed with dilute ammonium hydroxide and water, and the benzene was removed by distillation in vacuo. The oily residue was taken up in ether from which it crystallized. The precipitate was recrystallized twice from ether to yield 2-(4-chlorophenyl)-3-methyl-4-metathiazanone.
A solution of 11.2 g of potassium permanganate in 100 ml of warm water was added dropwise to a well stirred solution of 10 g of 2-(4-chlorophenyl)-3- methyl-4-metathiazanone in 50 ml of glacial acetic acid. The temperature was kept below 30°C with external cooling. An aqueous sodium bisulfite solution was then added to remove the manganese dioxide. The thick whitish oil which separated was taken up in chloroform and the extract was washed with water. Removal of the chloroform by distillation in vacuo yielded an oily residue which solidified. The solid was recrystallized from isopropyl alcohol to give 5 gof the product, 2-(4-chlorophenyl)-3-methyl-4-metathiazanone-1,1-dioxide, MP 116.2° to 118.6°C (corr.).

Brand name

Trancopal (Sanofi Aventis).

Therapeutic Function

Tranquilizer

World Health Organization (WHO)

Chlormezanone is a sedative with antianxiety properties and a central skeletal muscle relaxant effect. It had already been falling into obsolescence for several years.

Synthesis

Chlormezanone, 2-(p-chlorophenyl)-tetrahydro-3-methyl-4H-1,3- tiazin-4-on-1,1-dioxide (5.2.8), is synthesized by joint condensation of mercaptopropionic acid, methylamine, and 4-chlorobenzaldehyde, evidently through the intermediate stage of formation of 4-chlorobenzylidenemethylamine, giving the aminothioacetal 2- (p-chlorophenyl)-tetrahydro-3-methyl-4H-1,3-tiazin-4-one (5.2.7). Oxidation of the sulfur atom using potassium permanganate gives chlormezanone (5.2.8) [62,63].

Synthesis_80-77-3

storage

Room temperature

Spectrum Detail

Supplier

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