Veratraldehyde → 5-[(3,4-Dimethoxyphenyl)methylidene]imidazolidine-2,4-dione

HRID 444527Notes

Reaction equation

HRID 444527 reaction equation
[CH:1](=O)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.[NH:13]1[CH2:19][C:17](=[O:18])[NH:16][C:14]1=[O:15].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH:1]=[C:19]1[NH:13][C:14](=[O:15])[NH:16][C:17]1=[O:18]

Participants

5

Reactant 3

HCID 8419VeratraldehydeHCID 10006HydantoinHCID 517045Sodium Acetate

Product 1

HCID 1657985-[(3,4-Dimethoxyphenyl)methylidene]imidazolidine-2,4-dioneYield 38%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A magnetically stirred mixture of veratraldehyde (9.00 g., 93% pure), hydantoin (5.00 g.), fused, anhydrous sodium acetate (10 g.) and glacial acetic acid (20 ml) was refluxed (bath temperature 160°-165°) for 1.5 hours (solution within 5 minutes, crystallization during heating period). On cooling, water was added. The mixture was stirred for 1 hour, refrigerated 2 hours, filtered, washed with water and dried overnight at 55°/10 mm. The title compound was obtained as a yellow solid: 4.72 g. (38% yield) m.p. 280°-282°.

Workup

  1. custom(solution within 5 minutes, crystallization during heating period)
  2. temperatureOn cooling
  3. additionwater was added
  4. filtrationfiltered
  5. washwashed with water
  6. customdried overnight at 55°/10 mm

Sources & evidence

ORD record
ord-f88b0dc446e74d4185b9c315759c9e63
Source dataset
uspto-grants-1981_04
Patent number
US04264617

Reaction notes

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