1-Phenyl-1,2-propanedione → ethyl N-(1-benzoylvinyl)carbamate

HRID 1277351Notes

Reaction equation

HRID 1277351 reaction equation
O=[C:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C(NC(=O)O)C.[NH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>C1(C=CC(O)=CC=1)O.C1(C)C=CC=CC=1>[C:3]([C:2]([NH:18][C:19](=[O:20])[O:21][CH2:22][CH3:23])=[CH2:11])(=[O:4])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 113631-Phenyl-1,2-propanedioneHCID 86737834Urethane (ethyl carbamate)

Product 1

HCID 23453602ethyl N-(1-benzoylvinyl)carbamateYield 22.5%

Reagents, catalysts & solvents 2

HCID 785HydroquinoneCatalystHCID 1140TolueneSolvent

Procedure

In a flame dried nitrogen purged 100 ml round bottom flask equipped with a magnetic stirring bar, Dean-Stark trap and a reflux condenser were added 3.0 g (20.3 mmol) α-keto-propiophenone, 3.6 g (40.5 mmol) urethane (ethyl carbamate),10 mg (0.1 mmol) hydroquinone, 60 mg (0.3 mmol) paratoluenesulfonic acid and 20 ml of toluene. The mixture was refluxed under nitrogen with vigorous stirring for 31/2 hours. The solvent was removed under reduced pressure and the residue distilled through a short path distillation column giving approximately 1 g of ethyl N-(1-benzoylvinyl)carbamate bp≃130°-135° C. (1mm).

Workup

  1. customIn a flame dried nitrogen purged 100 ml round bottom flask
  2. customequipped with a magnetic stirring bar
  3. temperatureThe mixture was refluxed under nitrogen
  4. customThe solvent was removed under reduced pressure
  5. distillationthe residue distilled through a short path distillation column

Sources & evidence

ORD record
ord-12e66ad638d7439a962216cc638cdf47
Source dataset
uspto-grants-1981_07
Patent number
US04277420

Reaction notes

Loading…