TRANS-3-BROMO-N-ETHYLCINNAMAMIDE Struktur

TRANS-3-BROMO-N-ETHYLCINNAMAMIDE

Bezeichnung:TRANS-3-BROMO-N-ETHYLCINNAMAMIDE

CAS-Nr58473-74-8

Englisch Name:TRANS-3-BROMO-N-ETHYLCINNAMAMIDE

CBNumberCB2477363

SummenformelC11H12BrNO

Molgewicht254.12

MOL-Datei58473-74-8.mol

TRANS-3-BROMO-N-ETHYLCINNAMAMIDE physikalisch-chemischer Eigenschaften

Schmelzpunkt	89-91 °C(lit.)
Siedepunkt	417.5±45.0 °C(Predicted)
Dichte	1.369±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	14.59±0.46(Predicted)
Farbe	Pale Beige
Merck	13,2334

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26
WGK Germany	2
RTECS-Nr.	UC6314000
Toxizität	LD50 in mice (mg/kg): 660 ±28 i.p.; 2277 ±250 orally (Soroko)

Gefahreninformationscode (GHS)

TRANS-3-BROMO-N-ETHYLCINNAMAMIDE Chemische Eigenschaften,Einsatz,Produktion Methoden

Originator
Cinromide,ZYF Pharm Chemical
Verwenden
Cinromide is an anticonvulsant.
Verwenden
bone resorption inhibitor, farnesyldiphosphate synthetase inhibitor, antimetastatic
Definition
ChEBI: Cinromide is a member of cinnamamides and a secondary carboxamide.
Manufacturing Process
3-Bromo-N-ethylcinnamamide: I). A solution of trans-3-bromocinnamoyl chloride (12.3 g) in anhydrous toluene (150 ml) was added slowly with stirring to a solution of ethylamine (10 g) in dry ether (100 ml) at room temperature. The reaction mixture was heated at reflux for 1 hour, and the solvent and excess amine were then removed under reduced pressure. The residue was triturated with water, filtered, and recrystallized from ethanol-water to give trans-3-bromo-Nethylcinnamamide, m.p. 89-90°C, as a white crystalline material. NMR and IR spectra as well as elemental analysis were consistent with the assigned
II). trans-m-Bromocinnamic acid (14.8 g), ethanol (173 ml) and concentrated sulfuric acid (0.4 ml) were combined and heated at reflux for 15 hours. About 150 ml of the ethanol was distilled off, and the remaining solution was poured into ice/water (140 ml). The cold mixture was made strongly alkaline with 40% sodium hydroxide and extracted with methylene chloride (4x60 ml). The combined methylene chloride extract was dried over anhydrous potassium carbonate. The potassium carbonate was removed by filtration and the solvent stripped off under reduced pressure. trans-ethyl-3-Bromocinnamate, was obtained as a partially solidified oil. (IR spectrum was consistent with this compound).
trans-Ethyl-3-bromocinnamate (8.4 g), ethylamine (6.7 g), methanol (18 ml) and 4A molecular sieves (1 g) were combined and heated at reflux for ? hour. The mixture was cooled to about 45°C and sodium methylate (0.6 g) added. The mixture was then heated at reflux 1? hour and then cooled. It was acidified with concentrated hydrochloric acid (12 ml). The sieves were removed by filtration. Ice water was added to the filtrate to precipitate trans 3-bromo-N-ethylcinnamamide, m.p. 89-90°C (after recrystallization from ethanol/water)
Therapeutic Function
Anticonvulsant, Antiepileptic

TRANS-3-BROMO-N-ETHYLCINNAMAMIDE Upstream-Materialien And Downstream Produkte

TRANS-3-BROMO-N-ETHYLCINNAMAMIDE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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