TRANS-3-BROMO-N-ETHYLCINNAMAMIDE Chemical Properties

Melting point:

89-91 °C(lit.)

Boiling point:

417.5±45.0 °C(Predicted)

Density 

1.369±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

14.59±0.46(Predicted)

color 

Pale Beige

Merck 

13,2334

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

2

RTECS 

UC6314000

Toxicity

LD50 in mice (mg/kg): 660 ±28 i.p.; 2277 ±250 orally (Soroko)

MSDS

• Language:English Provider:SigmaAldrich

TRANS-3-BROMO-N-ETHYLCINNAMAMIDE Usage And Synthesis

Originator

Cinromide,ZYF Pharm Chemical

Uses

bone resorption inhibitor, farnesyldiphosphate synthetase inhibitor, antimetastatic

Uses

Cinromide is an anticonvulsant.

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

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