3-Phenylprop-2-Enal → Cinnamaldehyde, thiosemicarbazone

HRID 1856381Notes

Reaction equation

HRID 1856381 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH:6](=O)[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)C>O>[CH:6](=[N:1][NH:2][C:3]([NH2:5])=[S:4])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 702EthanolHCID 2723789Thiosemicarbazide

Product 1

HCID 2737765Cinnamaldehyde, thiosemicarbazone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 18.2 g (0.20 m) of thiosemicarbazide in 250 ml of hot water was gradually added to a solution of 26.4 g (0.20 m) of cinnamaldehyde in 250 ml of hot 2B ethanol. Small, colorless crystals began to ppt from the homogeneous mixture after several minutes of heating on a steam bath. Heating was continued for a half an hour, after which the mixture was cooled to room temperature and the product was collected by filtration, washed with cold ethanol, and air-dried to yield 25.5 g of small, pale yellow crystals. An additional 18.3 g of product was recovered by concentrating the mother liquors. Recrystallization from ethanol gave 29.3 g (0.14 m) of small, pale yellow crystals, m.p. 137°-139° C.

Workup

  1. waitto ppt from the homogeneous mixture after several minutes
  2. temperatureof heating on a steam bath
  3. temperatureHeating
  4. waitwas continued for a half an hour
  5. filtrationthe product was collected by filtration
  6. washwashed with cold ethanol
  7. customair-dried
  8. customto yield 25.5 g of small, pale yellow crystals
  9. customAn additional 18.3 g of product was recovered
  10. concentrationby concentrating the mother liquors
  11. customRecrystallization from ethanol
  12. customgave 29.3 g (0.14 m) of small, pale yellow crystals, m.p. 137°-139° C.

Sources & evidence

ORD record
ord-bbde15da2f904e8abc541e1519ad99bb
Source dataset
uspto-grants-1980_08
Patent number
US04219475

Reaction notes

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