Diethyl 5-hydantoylphosphonate → 5-[(2,3-Dimethyl-6-nitrophenyl)methylidene]imidazolidine-2,4-dione

HRID 979519Notes

Reaction equation

HRID 979519 reaction equation
[Na].[O:2]=[C:3]1[NH:7][C:6](=[O:8])[CH:5](P(OCC)(=O)OCC)[NH:4]1.[CH3:17][C:18]1[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]([N+:27]([O-:29])=[O:28])[C:19]=1[CH:20]=O>C(O)C.O>[CH3:17][C:18]1[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]([N+:27]([O-:29])=[O:28])[C:19]=1[CH:20]=[C:5]1[NH:4][C:3](=[O:2])[NH:7][C:6]1=[O:8]

Participants

6

Reactant 3

HCID 3516088Diethyl 5-hydantoylphosphonateHCID 5360545SodiumHCID 139370202,3-Dimethyl-6-nitrobenzaldehyde

Product 1

HCID 544700675-[(2,3-Dimethyl-6-nitrophenyl)methylidene]imidazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium (0.41 g, 0.018 g atom) was dissolved in ethanol (40 mL) and diethyl 2,4-dioxoimidazolidine-5-phosphonate (4.21 g, 18 mmol) added. After 5 minutes, 2,3-dimethyl-6-nitrobenzaldehyde (2.66 g, 15 mmol) was added in one portion and the mixture stirred at room temperature for 90 minutes. The mixture was diluted with water, filtered and the solid washed with water and air dried gave 5-[(2,3-dimethyl-6-nitrophenyl)methylene]-2,4-imidazolidinedione as a single geometrical isomer (3.35 g, 86%). Analytical sample prepared by crystallization from methanol had m.p. 293°-295° C.

Workup

  1. filtrationfiltered
  2. washthe solid washed with water and air
  3. customdried

Sources & evidence

ORD record
ord-3f0028703f8e4fcb9bb0ab98b8801e64
Source dataset
uspto-grants-1987_05
Patent number
US04668686

Reaction notes

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