Diethyl 5-hydantoylphosphonate → HCID 54280575, compound

HRID 867475Notes

Reaction equation

HRID 867475 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][CH:18]([N:20]1[CH2:24][CH:23]([CH2:25][O:26][C:27]2[CH:28]=[CH:29][C:30]([N+:35]([O-:37])=[O:36])=[C:31]([CH:34]=2)[CH:32]=O)[O:22][C:21]1=[O:38])[CH3:19]>C(O)C.O>[CH3:19][CH:18]([N:20]1[CH2:24][CH:23]([CH2:25][O:26][C:27]2[CH:28]=[CH:29][C:30]([N+:35]([O-:37])=[O:36])=[C:31]([CH:32]=[C:5]3[NH:4][C:3](=[O:2])[NH:7][C:6]3=[O:8])[CH:34]=2)[O:22][C:21]1=[O:38])[CH3:17]

Participants

6

Reactant 3

HCID 3516088Diethyl 5-hydantoylphosphonateHCID 5360545SodiumHCID 14281044HCID 14281044, compound

Product 1

HCID 54280575HCID 54280575, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium (0.9 g, 0.04 g atom) was dissolved in ethanol (150 mL) and diethyl 2,4-dioxoimidazolidine-5-phosphonate (9.19 g, 40 mmol) added. After 30 minutes solid 5-[[[3-(1-methylethyl)-2-oxooxazolidin-5-yl]methyl]oxy]-2-nitrobenzaldehyde (10.0 g, 32 mmol) was added and the mixture stirred vigorously. After 30 minutes, the mixture was diluted with water (150 mL) filtered and the solid washed with water and air dried to give 5-[[5-[[[3-(1-methylethyl)-2-oxooxazolidin-5-yl]methyl]oxy]-2-nitrophenyl]methylene]-2,4-imidazolidinedione (9.80 g, 77%). An analytical sample was prepared by crystallization from dimethylformamide and wate and had an m.p. 285°-287° C. (dec.).

Workup

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

Sources & evidence

ORD record
ord-af28b825ddcd4a21a0bf8b72651d6423
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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