Potassium Iodide → Phosphoric Acid di-tert-butyl Ester 2,5-dioxo-4,4-diphenyl-imidazolidin-1-ylmethyl Ester

HRID 1383750

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-:34])([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].[K+].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[O:21]=[C:4]1[NH:5][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)[C:7](=[O:8])[N:3]1[CH2:2][O:34][P:22](=[O:23])([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

35.5 Grams of 3-(chloromethyl)-5,5-diphenyl-2,4-imidazolidinedione from Step (A), 30.7 g of potassium di(t-butyl) phosphate, 0.6 g of potassium carbonate, and 0.15 g of potassium iodide were slurried into 200 mL acetonitrile. The reaction mixture was heated at reflux for 2.5 hours. The solution was filtered to remove potassium chloride precipitate. The filtrate was cooled to 0° C. and filtered to give 22.3 g of the title compound (38.6% yield); mp 108.5° C. (d). 1H NMR (DMSO-d6): 1.3 ppm (s, 18H), 5.2 (d, 2H), 7.3-7.5 (m, 10H), 9.9 (s, 1H); doublet from long range phosphorus coupling.

Aufarbeitung

temperatureThe reaction mixture was heated
temperatureat reflux for 2.5 hours
filtrationThe solution was filtered
customto remove potassium chloride precipitate
filtrationfiltered

Quellen und Nachweise

ORD-Eintrag: ord-92da913ed7284ceca65d24fa3ae26c6d
Quelldatensatz: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06255492B1

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