Potassium Iodide → HCID 54052585, compound

HRID 867476Notes

Reaction equation

HRID 867476 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=O.[CH2:13]([O:15][CH2:16][CH2:17]Br)[CH3:14].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[O-]CC.[Na+].[O:31]=[C:32]1[NH:36][C:35](=[O:37])[CH:34](P(OCC)(=O)OCC)[NH:33]1>O.C(O)C.Cl.CN(C)C=O>[CH2:13]([O:15][CH2:16][CH2:17][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:7]=[C:34]2[NH:33][C:32](=[O:31])[NH:36][C:35]2=[O:37])[CH:9]=1)[CH3:14]

Participants

11

Reactant 6

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 611412-Bromoethyl ethyl etherHCID 2723922Sodium ethoxideHCID 3516088Diethyl 5-hydantoylphosphonate

Product 1

HCID 54052585HCID 54052585, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-hydroxy-2-nitrobenzaldehyde (1.00 g, 6 mmol), 2-bromoethyl ethyl ether (1.00 g, 0.74 mL, 6.5 mmol), powdered potassium carbonate (0.91 g, 6.5 mmol), potassium iodide (catalytic quantity) and dimethylformamide (10 mL) was heated with stirring at 110° C. After 30 minutes, the mixture was cooled, diluted with water and extracted with dichloromethane (3 times). Combined extracts were washed with water (2 times), dried over sodium thiosulfate and concentrated in vacuo to leave an oil which was dissolved in ethanol (3 mL) and added to a stirred solution of sodium ethoxide (0.53 g, 78 mmol) and diethyl 2,4-dioxoimidazolidine-5-phosphonate (1.83 g, 77 mmol) in ethanol (15 mL). After 10 minutes, the mixture was diluted with 2N hydrochloric acid solution and the solid filtered off and dried in air to give 5-[[5-(2-ethoxyethoxy)-2-nitrophenyl]methylene]-2,4-imidazolidinedione as a partial hydrate (1.40 g, 73%), m.p. 228°-233° C. (dec.).

Workup

  1. temperaturewas heated
  2. temperaturethe mixture was cooled
  3. extractionextracted with dichloromethane (3 times)
  4. washCombined extracts were washed with water (2 times)
  5. dry with materialdried over sodium thiosulfate
  6. concentrationconcentrated in vacuo
  7. customto leave an oil which
  8. waitAfter 10 minutes
  9. filtrationthe solid filtered off
  10. customdried in air

Sources & evidence

ORD record
ord-8fbd03f2120449818a79c1047e083b6c
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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