N-Ethyl-N-3-((3-dimethylamino-1-oxo-2-propenyl)phenyl)acetamide

N-Ethyl-N-3-((3-dimethylamino-1-oxo-2-propenyl)phenyl)acetamide Property

Melting point:

111.0 to 115.0 °C

Boiling point:

400.7±45.0 °C(Predicted)

Density 

1.087±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Dichloromethane

form 

powder to crystal

pka

6.40±0.70(Predicted)

color 

Light orange to Yellow to Green

CAS DataBase Reference

96605-66-2(CAS DataBase Reference)

Safety

HS Code 

29242990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H227Combustible liquid

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P262Do not get in eyes, on skin, or on clothing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P370+P378In case of fire: Use … for extinction.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

N-Ethyl-N-3-((3-dimethylamino-1-oxo-2-propenyl)phenyl)acetamide Chemical Properties,Usage,Production

Uses

An impurity and intermediate of Zaleplon production.It is used as a reagent in the preparation of immunogens for immunodetection and quantification of pyrazolopyrimidine sedatives.

Synthesis

1. Acetamidoacetophenone (0.2 g, 1.13 mmol) was dissolved in acetone (2 mL), potassium hydroxide (63 mg, 1.13 mmol) was added, followed by ethyl iodide (0.45 mL, 5.64 mmol). After stirring at room temperature overnight, the reaction mixture was concentrated to dryness. The residue was redissolved in ethyl acetate, washed sequentially with water and brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give N-(3-acetylphenyl)-N-ethylacetamide as an orange powder (0.23 g, 100%) with a melting point of 203-204 °C. 2. The above product (0.23 g, 1.13 mmol) was dissolved in acetonitrile (2 mL), N,N-dimethylformamide dimethyl acetal (150 μL, 0.12 mmol) was added, and the reaction was carried out in a microwave reactor at 180 °C for 10 min. After evaporation of the solvent, the residue was filtered and washed with ethyl acetate/petroleum ether (1:3) to afford N-[3-(3-dimethylaminopropenoyl)phenyl]-N-ethylacetamide as an orange solid (0.30 g, 100%). 3. The above substance (0.228 g, 0.88 mmol), 4-hydroxyphenylguanidine nitrate (0.188 g, 0.88 mmol) and sodium hydroxide (35 mg, 0.88 mmol) were mixed in acetonitrile (2 mL), and heated in a microwave reactor for 15 min at 190 °C. After evaporation of the solvent, the residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether, 1:1) to afford N-ethyl-N-3-[(3-dimethylamino-1-oxo-2-propenyl)phenyl]-acetamide as a yellow solid (117 mg, 38%).

References

[1] Patent: WO2005/12262, 2005, A1. Location in patent: Page/Page column 45-46
[2] Patent: CN105622615, 2016, A. Location in patent: Paragraph 0128; 0129; 0130; 0131