Hydrochloric Acid → HCID 20137559, compound

HRID 1253316Notes

Reaction equation

HRID 1253316 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[CH2:6][CH3:7].[C:16](Cl)(=[O:19])[CH2:17][CH3:18].Cl>C(=S)=S>[C:5]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:19])[CH2:17][CH3:18])=[CH:12][CH:11]=1)(=[O:8])[CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 121072-MethylacetanilideHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20137559HCID 20137559, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Aluminum chloride (600 g, 4.50 mol) is added in portion to a cold (0°-10° C.) stirred solution of propionanilide (230 g, 1.54 mol) and of propionyl chloride (297 g, 3.2 mol) in carbon disulphide (600 ml). The reaction mixture is heated at reflux for 24 h. It is poured into a mixture of hydrochloric acid and crushed ice, and extracted with methylene chloride. The organic phase is washed with a 1% sodium hydrogen carbonate solution, with water, dried (Na2SO4) and filtered. Evaporation of the solvent under reduced pressure gives 1-(4'-propionamidophenyl)-propan-1-one (165 g, 0.8 mol, yield 52%) m.p. 154°-155° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 24 h
  3. customcrushed ice
  4. extractionextracted with methylene chloride
  5. washThe organic phase is washed with a 1% sodium hydrogen carbonate solution, with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b6d2929369234783aef361a641d7b192
Source dataset
uspto-grants-1988_05
Patent number
US04748253

Reaction notes

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