3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE

3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE Basic information
Product Name:3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE
Synonyms:TRIMETHADIONE;3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE;3,5,5-TRIMETHYLOXOZOLIDINE-2,4-DIONE;3,5,5-Trimethyl-2,4-dioxooxazolidine;2,4-Oxazolidinedione, 3,5,5-trimethyl-;3,3,5-Trimethyl-2,4-diketooxazolidine;3,5,5-Trimethyl-1,3-oxazolidine-2,4-dione;3,5,5-Trimethyl-2,4-oxazolidinedione
CAS:127-48-0
MF:C6H9NO3
MW:143.14
EINECS:204-845-8
Product Categories:
Mol File:127-48-0.mol
3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE Structure
3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE Chemical Properties
Melting point 45-46°C
Boiling point 78-80°C 5mm
density 1.3075 (rough estimate)
refractive index 1.4290 (estimate)
Fp 78-80°C/5mm
storage temp. Inert atmosphere,Room Temperature
solubility Soluble in water, very soluble in ethanol (96 per cent).
pka-2.18±0.40(Predicted)
form neat
color White to Off-White
Water Solubility Soluble in water 50 g/L.
Merck 14,9706
BRN 121627
CAS DataBase Reference127-48-0(CAS DataBase Reference)
EPA Substance Registry SystemTrimethadione (127-48-0)
Safety Information
Hazard Codes T
Risk Statements 61-20/21/22
Safety Statements 53-22-36/37/39-45
WGK Germany 3
RTECS RQ2100000
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE Usage And Synthesis
Chemical PropertiesWhite, granular, crystalline substance; camphor-like odor. Soluble in water; freely soluble in alcohol, chloroform, and ether; pH 6.0 (5% solution).
OriginatorTridione,Abbott,US,1946
Usesantifungal
UsesTrimethadione is used in minor forms of epilepsy that does not respond to treatment of other drugs.
Uses3,5,5-Trimethyloxazolidine-2,4-dione is used in the control of absence (petit mal) seizures that are refractory to treatment with other medications. It is used in the treatment of epilepsy.
DefinitionChEBI: Trimethadione is an oxazolidinone that is 1,3-oxazolidine-2,4-dione substituted by methyl groups at positions 3, 5 and 5. It is an antiepileptic agent. It has a role as a geroprotector and an anticonvulsant.
Manufacturing ProcessTo a cooled solution of 23 parts of sodium in 400 parts of dry ethanol are added 60 parts of dry urea and 132 parts of ethyl α-hydroxy-isobutyrate. The mixture is heated on a steam bath under reflux for about 16 hours and the liberated ammonia is removed from the solution by drawing a current of dry air through it at the boiling point. The solution of the sodium salt of 5,5- dimethyloxazolidine-2,4-dione so obtained is cooled and treated with 284 parts of methyl iodide. The mixture is allowed to stand at room temperature for 3 days, excess methyl iodide and ethanol are then removed by distillation under reduced pressure.
The residue is dissolved in ether and the solution is washed with sodium chloride solution and then with a little sodium thiosulfate solution. The ethereal solution is dried over sodium sulfate and ether removed by distillation. A yield of 108 parts of 3,5,5-trimethyloxazolidine-2,4-dione is obtained having a melting point of 45° to 46°C with slight softening at 43°C. This represents a 75% theory yield on the ethyl α-hydroxy-iso-butyrate taken. The product may be further purified by dissolving the minimum quantity of dry ether and cooling to -10°C. The product so obtained melts sharply at 45.5° to 46.5°C according to US Patent 2,559,011.
Brand nameTridione (Abbott).
Therapeutic FunctionAnticonvulsant
Synthesis Reference(s)Tetrahedron, 51, p. 5891, 1995 DOI: 10.1016/0040-4020(95)00257-9
HazardMay have adverse side effects; toxic in overdose.
Clinical UseTrimethadione is indicated only for control of absence seizures refractory to treatment with other AEDs. It is ineffective against other seizure types. Trimethadione is a pro-drug and is metabolized by N-demethylation to dimethadione, which is effective in the pentylenetetrazole test, which acts by decreasing T-type calcium currents. Trimethadione is rapidly absorbed, is not protein bound, and has a half-life of 16 to 24 hours. The half-life of dimethadione, however, is substantially longer (i.e., 6–13 days), and dimethadione accumulates to concentrations greater than the parent drug. Because of its potentially fatal side effects. including aplastic anemia, nephrosis, idiosyncratic rashes, and exfoliative dermatitis, trimethadione rarely is used today.
SynthesisTrimethadione, 3,5,5-trimethyloxazolidine-2,4-dione (9.8.2), is synthesized by methylating 5,5-trimethyloxazolidine-2,4-dione (9.8.1) with dimethylsulfate.Starting 5,5-trimethyloxazolidine-2,4-dione (9.8.1) is in turn synthesized by the cyclocondensation of the ester of 2-hydroxyisobutyric acid with urea [26¨C28].

Synthesis_127-48-0

carfentrazone-ethyl Gabapentin LACOSAMIDE Sodium 2-propylpentanoate Metribuzin Triazophos Dichlozolinate Docetaxel Metabolite M4 Dichlozoline 3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE 2,4-Oxazolidinedione, 3-(3,5-dichlorophenyl)-5-methyl-5-oxiranyl- VINCLOZOLIN 3-(2-AMINO-ETHYL)-5,5-DIMETHYL-OXAZOLIDINE-2,4-DIONE HYDROCHLORIDE vinzolidine 3-(2-AMINO-ETHYL)-1-OXA-3-AZA-SPIRO[4.4]NONANE-2,4-DIONE HYDROCHLORIDE HOY-DIMETHADIONE-2-14C PARAMETHADIONE (500 MG) 3-ethyl-5,5-dimethyloxazolidine-2,4-dione

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