Hydrochloric Acid → 3-(4-Acetylphenyl)-N-(2-hydroxyethyl)prop-2-enamide

HRID 1981152Notes

Reaction equation

HRID 1981152 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].S(Cl)(Cl)=O.[CH2:19]([CH2:21][NH2:22])[OH:20].Cl>O1CCOCC1.C1C=CC=CC=1>[OH:20][CH2:19][CH2:21][NH:22][C:10](=[O:12])[CH:9]=[CH:8][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 24386Thionyl ChlorideHCID 566282613-(4-Acetylphenyl)prop-2-enoic acid

Product 1

HCID 536510963-(4-Acetylphenyl)-N-(2-hydroxyethyl)prop-2-enamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 9.5 g (0.05 mole) of 4-acetylcinnamic acid [obtained according to G. H. Cleland, J. Org. Chem., 34, 744 (1969)], of 30 g of thionyl chloride and 40 cc of benzene was brought to reflux for 20 minutes. The solution was concentrated dry under low pressure. The residual solid was dissolved in 100 cc of dioxane and the resulting solution was added, dropy by drop at a temperature of 20° C., to a solution of 9.3 g (0.15 mole) of ethanolamine in 50 cc of dioxane. The mixture was stirred for 1 hour at room temperature, poured into a mixture of 500 g of ice and 20 cc of 10N hydrochloric acid then extracted with chloroform. The organic phase was washed with water and dried on sodium sulfate. By evaporation of the solvent under low pressure there was obtained N-(2-hydroxyethyl)-4-acetylcinnamamide which was purified by recrystallization in ethylacetate. Melting point=124°-125° C. Yield: 4.2 g (36% of theory).

Workup

  1. temperatureto reflux for 20 minutes
  2. concentrationThe solution was concentrated
  3. customdry under low pressure
  4. dissolutionThe residual solid was dissolved in 100 cc of dioxane
  5. additionthe resulting solution was added
  6. customat a temperature of 20° C.
  7. extractionthen extracted with chloroform
  8. washThe organic phase was washed with water
  9. customdried on sodium sulfate
  10. customBy evaporation of the solvent under low pressure there

Sources & evidence

ORD record
ord-9685bf8700a14616a39d1a35e37a4a2f
Source dataset
uspto-grants-1985_04
Patent number
US04512994

Reaction notes

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