1,2,4-Trichlorobenzene → N-[4-(1-oxopropyl)phenyl]acetamide

HRID 653552Notes

Reaction equation

HRID 653552 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:11](Cl)(=[O:14])[CH2:12][CH3:13].ClC1C=CC(Cl)=CC=1Cl.[Cl-].[Cl-].[Cl-].[Al+3]>C(O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][CH3:13])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 131,2,4-TrichlorobenzeneHCID 904AcetanilideHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 85655N-[4-(1-oxopropyl)phenyl]acetamideYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Acetanilide (13.94 g), propionyl chloride (14.31 g) and 1,2,4-trichlorobenzene (100 ml) were warmed to 60° C. and aluminium trichloride (40.0 g) was added over 15 minutes. The mixture was heated at 100° C. for 90 minutes, cooled at 40° C. and ethanol (200 ml) was added dropwise keeping the temperature below 60° C. by means of an ice-water bath. After stirring for 30 minutes at 40° C. a homogeneous system was obtained. This was quenched with water (100 ml) at 25°-30° C. and stirred for 15 minutes. Dichloromethane (300 ml) and water (200 ml) were added and the organic layer was separated and washed with water (2×200 ml). The organic layer was evaporated to about half-volume (about 150 ml), and petroleum ether (60° C.-80° C.) (150 ml) was added at 50° C. A solid precipitated and was collected after 60 minutes of stirring to afford p-acetamidopropiophenone (15.12 g; 79%), m.p. 169°-70° C.

Workup

  1. temperaturecooled at 40° C.
  2. customthe temperature below 60° C.
  3. customwas obtained
  4. customThis was quenched with water (100 ml) at 25°-30° C.
  5. stirringstirred for 15 minutes
  6. additionDichloromethane (300 ml) and water (200 ml) were added
  7. customthe organic layer was separated
  8. washwashed with water (2×200 ml)
  9. customThe organic layer was evaporated to about half-volume (about 150 ml), and petroleum ether (60° C.-80° C.) (150 ml)
  10. additionwas added at 50° C
  11. customA solid precipitated
  12. customwas collected after 60 minutes
  13. stirringof stirring

Sources & evidence

ORD record
ord-98236826f70d48c5aa3226391acee7e2
Source dataset
uspto-grants-1987_06
Patent number
US04677228

Reaction notes

Loading…