Potassium Carbonate → Phosphoric Acid 2,5-dioxo-4,4-diphenyl-imidazolidin-1-ylmethyl Ester Dimethyl Ester

HRID 1383749

Reaktionsgleichung

Reaktionsgleichung von HRID 1383749
Cl[CH2:2][N:3]1[C:7](=[O:8])[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:4]1=[O:21].[P:22]([O-:28])([O:26][CH3:27])([O:24][CH3:25])=[O:23].[K+].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].C(#N)C>[CH3:25][O:24][P:22](=[O:23])([O:26][CH3:27])[O:28][CH2:2][N:3]1[C:7](=[O:8])[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:4]1=[O:21]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 110986333-(Chloromethyl)-5,5-diphenylimidazolidine-2,4-dioneHCID 23666574Dimethyl phosphate, potassium salt

Produkt 1

HCID 15459543Phosphoric Acid 2,5-dioxo-4,4-diphenyl-imidazolidin-1-ylmethyl Ester Dimethyl EsterAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Thirty grams of 3-(chloromethyl)-5,5-diphenyl-2,4-imidazolidinedione from Step (A), 17.1 g of potassium dimethyl phosphate, 0.6 g of potassium carbonate, and 0.15 g of potassium iodide were slurried into 75 mL of acetonitrile. The reaction mixture was heated at reflux for 3 hours. The solution was filtered to remove potassium chloride precipitate and concentrated to thick oil. Isopropyl alcohol was added to the oil and cooled to 0° C. The product was filtered and dried under vacuum. Sixteen grams of the title compound was obtained (40.9% yield); mp 123.1-124.3° C. Proton nuclear magnetic resonance spectroscopy (1H NMR) deuterated dimethyl sulfoxide (DMSO-d6): 3.6 ppm (d, 6H), 5.3 (d, 2H), 7.3-7.5 (m, 10H), 10.0 (s, 1H); doublets from long range phosphorous coupling.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe solution was filtered
  4. customto remove potassium chloride precipitate
  5. concentrationconcentrated to thick oil
  6. additionIsopropyl alcohol was added to the oil
  7. filtrationThe product was filtered
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-39384ed111e54056b81ed90d5be2440e
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255492B1

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