Sodium Iodide → diethyl ((1-(triphenylmethyl)-1H-imidazol-4-yl)methyl)phosphonate

HRID 1068431Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([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)[CH:7]=1.[P:27]([O:34]CC)([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30].[I-].[Na+]>C(#N)C>[CH2:29]([O:28][P:27]([CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([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)[CH:7]=1)([O:31][CH2:32][CH3:33])=[O:34])[CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

The product from Step C is dissolved in acetonitrile and cooled to 0° C. Triethyl phosphite (1 equivalent) and sodium iodide (1 equivalent) are added, and the reaction stirred at room temperature overnight. The reaction is quenched with ammonium chloride, and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and concentrated to provide the title compound.

Workup

customThe reaction is quenched with ammonium chloride
extractionextracted with ethyl acetate
dry with materialThe organic phase is dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-cac0de4c6d3d4811ba0d045afa69d729
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248756B1

Reaction notes

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