Trimethobenzamid

Bezeichnung:Trimethobenzamid

CAS-Nr138-56-7

Englisch Name:Trimethobenzamide

CBNumberCB5700149

SummenformelC21H28N2O5

Molgewicht388.46

MOL-Datei138-56-7.mol

Synonyma

Trimethobenzamid

Trimethobenzamid physikalisch-chemischer Eigenschaften

storage temp.	2-8°C
pka	pKa 8.27±0.03(H2O) (Uncertain)
NIST chemische Informationen	Benzamide, n-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxy-(138-56-7)

Sicherheit

Giftige Stoffe Daten

138-56-7(Hazardous Substances Data)

Trimethobenzamide Chemische Eigenschaften,Einsatz,Produktion Methoden

Originator
Tigan,Beecham,US,1973
Verwenden
Antiemetic.
Definition
ChEBI: The amide obtained by formal condensation of 3,4,5-trihydroxybenzoic acid with 4-[2-(N,N-dimethylamino)ethoxy]benzylamine. It is used to prevent nausea and vomitting in humans.
Manufacturing Process
To 122 grams (1 mol) of p-hydroxybenzaldehyde in 1 liter of chlorobenzene were added 66 grams (1.04 mols) of sodium methoxide (85%) and 108 grams (1 mol) of 2-dimethylaminoethyl chloride. The mixture was stirred and refluxed for 15 hours, then cooled and the precipitated sodium chloride filtered off. The filtrate was concentrated at steam temperature under water vacuum and the residual oil was fractionated in high vacuum, to give 4-(2- dimethylaminoethoxy)benzaldehyde, BP2.2145°C.
Two teaspoons of Raney nickel catalyst were added to a solution of 65.6 grams (0.34 mol) of 4-(2-dimethylaminoethoxy)benzaldehyde in 300 ml of 10% ammoniacal ethanol. The mixture was hydrogenated at 80°C and a pressure of 1,000 psi. The catalyst was filtered off, the volatiles were distilled off and the residual oil was fractionated in high vacuum, to obtain 4-(2- dimethylaminoethoxy)benzylamine, BP0.3120° to 123°C.
To 9.7 grams (0.05 mol) of 4-(2-dimethylaminoethoxy)benzylamine, dissolved in 100 ml of acetonitrile, was added all at once 12 grams (0.051 mol) of 3,4,5-trimethoxybenzoyl chloride, dissolved in 75 ml of acetonitrile. The mixture was stirred and refluxed for 8 hours, and then cooled. The crystalline solid, which had formed, was filtered off, washed with acetonitrile and recrystallized from acetonitrile, to give 4-(2-dimethylaminoethoxy)-N-(3,4,5- trimethoxybenzoyl)benzylamine hydrochloride, MP 185° to 186°C.
Trademarks
Tigan (King).
Therapeutic Function
Antinauseant

Trimethobenzamide Upstream-Materialien And Downstream Produkte

Trimethobenzamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

138-56-7, Trimethobenzamide Verwandte Suche:

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