Trimethylsilyl iodide → [(2-Benzo[b]thiophenecarboxamido)methylene]bis(phosphonic acid)

HRID 1088604Notes

Reaction equation

[S:1]1[C:5]([C:6]([NH:8][CH:9]([P:18](=[O:25])([O:22]CC)[O:19]CC)[P:10](=[O:17])([O:14]CC)[O:11]CC)=[O:7])=[CH:4][C:3]2[CH:26]=[CH:27][CH:28]=[CH:29][C:2]1=2.I[Si](C)(C)C>C(Cl)Cl>[S:1]1[C:5]([C:6]([NH:8][CH:9]([P:18](=[O:19])([OH:22])[OH:25])[P:10](=[O:11])([OH:17])[OH:14])=[O:7])=[CH:4][C:3]2[CH:26]=[CH:27][CH:28]=[CH:29][C:2]1=2

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of tetraethyl [(2-benzo[b]thiophenecarboxamido)methylene]bis(phosphonate) (463 mg) in methylene chloride (2 ml) was added iodotrimethylsilane (1 ml) in one portion at 5° C. The mixture was stirred for one hour at 5° C., allowed to stand for 2 days in a refrigerator and then additionally stirred for one hour at ambient temperature. The mixture was extracted with water. The aqueous layer was washed with methylene chloride and diethyl ether and then evaporated under reduced pressure. The residue was dissolved in water and therein tert-butylamine (183 mg) was added. The mixture was lyophilized to give bis(tert-butylamine)-salt of [(2-benzo[b]thiophenecarboxamido)methylene]bis(phosphonic acid) (277 mg) as a white powder.

Workup

waitto stand for 2 days in a refrigerator
stirringadditionally stirred for one hour at ambient temperature
extractionThe mixture was extracted with water
washThe aqueous layer was washed with methylene chloride and diethyl ether
customevaporated under reduced pressure
dissolutionThe residue was dissolved in water
additiontert-butylamine (183 mg) was added

Sources & evidence

ORD record: ord-97091aca5c404a348876131b789ba8bc
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04963536

Reaction notes

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