Acetanilide → N-[4-(1-oxopropyl)phenyl]acetamide

HRID 1395087Notes

Reaction equation

HRID 1395087 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:7])[CH3:6].[C:15](Cl)(=[O:18])[CH2:16][CH3:17]>C(=S)=S>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:5](=[O:7])[CH3:6])=[CH:10][CH:11]=1)(=[O:18])[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 904AcetanilideHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 85655N-[4-(1-oxopropyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
25 °C

Procedure

1290 g of aluminium chloride (9.6 mole) were suspended with stirring in 1500 ml of carbon disulphide. 405 g of acetanilide (3 moles) were added slowly to this suspension, while the temperature was kept at 25° C. The reaction mixture was heated until reflux and was cooled immediately to 25° C. 565 ml of propionyl chloride (6.5 moles) were added dropwise in such a way that the temperature was kept at 25° C. The reaction mixture was heated until reflux for 5 hours and kept overnight at ambient temperature (20° C.). The supernatant carbon disulphide layer was decanted and the remaining viscous mixture was poured in a mixture of ice and hydrochloric acid. The residue formed was filtered off and further recrystallized from a mixture of 1500 ml of ethanol and 75 ml of water. Drying was applied under vacuum at 100° C. A light yellow powder was obtained.

Workup

  1. customwas kept at 25° C
  2. temperatureThe reaction mixture was heated
  3. temperatureuntil reflux
  4. customwas kept at 25° C
  5. temperatureThe reaction mixture was heated
  6. temperatureuntil reflux for 5 hours
  7. custom(20° C.)
  8. customThe supernatant carbon disulphide layer was decanted
  9. additionthe remaining viscous mixture was poured in a mixture of ice and hydrochloric acid
  10. customThe residue formed
  11. filtrationwas filtered off
  12. customfurther recrystallized from a mixture of 1500 ml of ethanol and 75 ml of water
  13. customDrying
  14. customwas applied under vacuum at 100° C
  15. customA light yellow powder was obtained

Sources & evidence

ORD record
ord-d07dcea0b1e44504ae6b7411e8226fad
Source dataset
uspto-grants-1980_05
Patent number
US04202697

Reaction notes

Loading…