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

HRID 1383750

Reaction equation

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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-92da913ed7284ceca65d24fa3ae26c6d
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255492B1

Linked notes

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