3-Phenylprop-2-Enal → HCID 965914, compound

HRID 1703626Notes

Reaction equation

HRID 1703626 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH:8](=O)[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(O)(=O)C>[CH:8](=[C:7]1[NH:1][C:2](=[O:3])[NH:4][C:5]1=[O:6])[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 962WaterHCID 10006Hydantoin

Product 1

HCID 965914HCID 965914, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of hydantoin (40 g), freshly distilled cinnamaldehyde (50 g), and fused sodium acetate (80 g) in acetic acid (160 ml) was heated to reflux for 11/2 hours. The solution was poured into cold water (1.5 l) to precipitate the orange product, which was removed by filtration. This product was washed with water until neutral and then with cold ethanol to give 69 g (85% theoretical yield) of virtually pure product. Before use, the product was recrystallised from ethanol to give yellow crystals of 5-cinnamylidenehydantoin, m.p. 268°-270° (decomp.), the infra-red spectrum of which showed the expected main peaks at 1750, 1700, 1640, 1390, 1350, 1020, 970, 895, 825, 750, 690, and 655 cm-1.

Workup

  1. temperatureto reflux for 11/2 hours
  2. customto precipitate the orange product, which
  3. customwas removed by filtration
  4. washThis product was washed with water until neutral and then with cold ethanol
  5. customto give
  6. custom69 g (85% theoretical yield) of virtually pure product
  7. customBefore use, the product was recrystallised from ethanol

Sources & evidence

ORD record
ord-86b80dc2f32946d2be3b5e7dfb31cab9
Source dataset
uspto-grants-1978_11
Patent number
US04124760

Reaction notes

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