Water → (Phenylsulfonylaminomethylene)bis(phosphonic acid)

HRID 1088605Notes

Reaction equation

HRID 1088605 reaction equation
[C:1]1([S:7]([NH:10][CH:11]([P:20](=[O:27])([O:24]CC)[O:21]CC)[P:12](=[O:19])([O:16]CC)[O:13]CC)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[Si](C)(C)C.O.C(Cl)(Cl)Cl>C(Cl)Cl>[C:1]1([S:7]([NH:10][CH:11]([P:20](=[O:21])([OH:27])[OH:24])[P:12](=[O:13])([OH:19])[OH:16])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 85247Trimethylsilyl iodideHCID 53933859HCID 53933859, compound

Product 1

HCID 10068042(Phenylsulfonylaminomethylene)bis(phosphonic acid)Yield 64.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tetraethyl (phenylsulfonylaminomethylene)bis(phosphonate) (400 mg) in methylene chloride (4 ml), was added iodotrimethylsilane (0.8 ml) dropwise with stirring under nitrogen gas atmosphere in an ice-water bath. The mixture was stirred for 30 minutes at the same condition and then at ambient temperature for 1.5 hours. To the reaction mixture were added water (10 ml) and chloroform (8 ml) under ice-water bath cooling. The separated aqueous layer was washed with chloroform until its color disappeared and then evaporated in reduced pressure. The residue was washed with ethanol to give white powder of (phenylsulfonylaminomethylene)bis(phosphonic acid) (194 mg).

Workup

  1. stirringThe mixture was stirred for 30 minutes at the same condition
  2. temperaturecooling
  3. washThe separated aqueous layer was washed with chloroform until its color
  4. customevaporated in reduced pressure
  5. washThe residue was washed with ethanol

Sources & evidence

ORD record
ord-e200b1765a9b495f960f71e9133eddc3
Source dataset
uspto-grants-1990_10
Patent number
US04963536

Reaction notes

Loading…