Trimethylsilyl iodide → HCID 19700501, compound

HRID 861886Notes

Reaction equation

I[Si](C)(C)C.[CH:6]1([C:12]2[CH:21]=[C:20]3[C:15]([CH2:16][CH2:17][C:18]([C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][P:32]([O:37]CC)([O:34]CC)=[O:33])=[CH:27][CH:26]=4)=[O:23])=[CH:19]3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>C(Cl)(Cl)(Cl)Cl>[CH:6]1([C:12]2[CH:21]=[C:20]3[C:15]([CH2:16][CH2:17][C:18]([C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][P:32]([OH:37])([OH:34])=[O:33])=[CH:27][CH:26]=4)=[O:23])=[CH:19]3)=[CH:14][CH:13]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

Conditions

Temperature: 0 °C

Procedure

Iodotrimethylsilane [(CH3)3SiI] (0.458 g) was added to a suspension of 7-cyclohexyl-N-(4-diethoxyphosphorylmethylphenyl)-3,4-dihydronaphthalene-2-carboxamide (0.5 g) in carbon tetrachloride (10 ml) at 0° C. After stirring at 0° C. for 1 hour and then at room temperature for 15 hours, this mixture was concentrated under reduced pressure. To the residue, methanol (6 ml) was added; this mixture was acidified with 1N HCl and stirred at room temperature for 30 minutes. The resulting crystals were collected by filtration and recrystallized from methanol-water to yield 7-cyclohexyl-N-(4-phosphonomethylphenyl)-3,4-dihydronaphthalene-2-carboxamide (0.28 g, 63%) as pale yellow prisms having a melting point of 203°-205° C.

Workup

waitat room temperature for 15 hours
concentrationthis mixture was concentrated under reduced pressure
additionTo the residue, methanol (6 ml) was added
stirringstirred at room temperature for 30 minutes
filtrationThe resulting crystals were collected by filtration
customrecrystallized from methanol-water

Sources & evidence

ORD record: ord-48e32cd2f2ae414ea263df18048a0a3b
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05716944

Reaction notes

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