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

HRID 377024

Reaktionsgleichung

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

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

temperatureThe reaction mixture was heated
temperatureat reflux for 3 hours
filtrationThe solution was filtered
customto remove potassium chloride precipitate
concentrationconcentrated to thick oil
additionIsopropyl alcohol was added to the oil
filtrationThe product was filtered
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-85d5aa90d7c74d0da7791aad0ed02f39
Quelldatensatz: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06022975

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