N-[4-(2-CHLOROPROPANOYL)PHENYL]ACETAMIDE Chemical Properties

Melting point:

119-120 °C(Solv: ethanol (64-17-5); water (7732-18-5))

Boiling point:

429.9±25.0 °C(Predicted)

Density 

1.237±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

14.47±0.70(Predicted)

N-[4-(2-CHLOROPROPANOYL)PHENYL]ACETAMIDE Usage And Synthesis

Synthesis

a) Synthesis of 1-(4-acetamidophenyl)-2-chloropropanone: 118 g (0.93 mol) of 2-chloropropionyl chloride was added slowly and dropwise over a period of 1.5 h to a mixture containing 69.2 g (0.50 mol) of N-phenylacetamide and 525 mL of carbon disulfide. Subsequently, 205 g (1.50 mol) of aluminum chloride was added to the reaction system and the mixture was heated to reflux for 1 hour. Upon completion of the reaction, the supernatant was decanted and the residue was hydrolyzed with 1900 mL of ice water and 385 mL of 4N hydrochloric acid. The precipitate formed was separated by filtration and the precipitate was dissolved in benzene. The benzene solution was azeotropically distilled using a Dean-Stark apparatus to remove water. The hot solution was treated with activated carbon (CXA) and cooled to give 102.4 g (yield: 90.82%) of the target compound 1-(4-acetamidophenyl)-2-chloropropanone as a micron colored powder. Melting point (Kofler assay): 120°C.

References

[1] Organic Letters, 2017, vol. 19, # 10, p. 2548 - 2551
[2] Patent: US5128349, 1992, A
[3] Patent: US4677228, 1987, A
[4] Patent: WO2018/86703, 2018, A1. Location in patent: Page/Page column 200
[5] Tetrahedron Letters, 1981, vol. 22, # 43, p. 4305 - 4308