Chlormezanone

Chlormezanone Basic information
Product Name:Chlormezanone
Synonyms:2-(4-Chlorophenyl)-3-methyl-1,3-thiazinan-4-one 1,1-dioxide;2-(4-Chlorophenyl)-3-methyl-4-metathiazanone-1,1-dioxide;2-(4-Chlorophenyl)-3-methyl-4-thiazanone 1,1-dioxide;2-(para-chlorophenyl)tetrahydro-3-methyl-4h-1,3-thiazin-4-one,1,1-dioxide;2-(p-chlorophenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide;2-(p-Chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one;2-(4-chlorophenyl)-3-methyl-1,1-dioxo-1,3-thiazinan-4-one;ChlorMezanone (Trancopal)
CAS:80-77-3
MF:C11H12ClNO3S
MW:273.74
EINECS:201-307-4
Product Categories:Trancopal
Mol File:80-77-3.mol
Chlormezanone Structure
Chlormezanone 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. Sealed in dry,Room Temperature
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 ReferenceChlormezanone(80-77-3)
Safety Information
RTECS XJ1050000
HS Code 2934.99.4400
Hazardous Substances Data80-77-3(Hazardous Substances Data)
MSDS Information
Chlormezanone Usage And Synthesis
OriginatorTrancopal,Winthrop-Breon,US,1958
UsesSkeletal muscle relaxant
UsesChlormezanone improves the emotional state of the patient, relieving moderate anxiety and stress. However, it has a number of side effects, and because it does not have any advantage over other anxiolytics, it is rarely used in practice.
UsesThe use of chlormezanone is associated with large increases in the risk of Stevens-Johnson syndrome or toxic epidermal necrolysis.
DefinitionChEBI: 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.
Manufacturing ProcessA 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 nameTrancopal (Sanofi Aventis).
Therapeutic FunctionTranquilizer
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.
Biological ActivityAnxiolytic and skeletal muscle relaxant that acts at the benzodiazepine site of GABA A receptors.
SynthesisChlormezanone, 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

storageRoom temperature
Chlormezanone Preparation Products And Raw materials
Raw materials4-Chlorobenzaldehyde-->3-Mercaptopropionic acid
Preparation Productswhitener WG for wool-->Ketamine hydrochloride
2-tert-Butyl-4,5-dichloro-3-2H-pyridazinone Chloromethyl chlorosulfate Bensulfuron methyl Chlortalidone Phthalhydrazide Buprofezin Thiamethoxam Chlorine dioxide Hydrochlorothiazide Benziothiazolinone Hexazinone Rutile Toltrazuril Chlormezanone Hexythiazox Quartz Methyl bromide sulfur dioxide

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.