Sodium Iodide → HCID 15786045, compound

HRID 1492907Notes

Reaction equation

HRID 1492907 reaction equation
[Cl:1][C:2]([Cl:19])([P:11](=[O:18])([O:15]CC)[O:12]CC)[P:3](=[O:10])([O:7]CC)[O:4][CH2:5][CH3:6].[Na+:20].[I-].C[Si](Cl)(C)C.ClC(Cl)(P(=O)(O[Si](C)(C)C)OCC)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C.[OH-].[Na+]>CC#N.CO.O>[Na+:20].[Na+:20].[Na+:20].[CH2:5]([O:4][P:3]([C:2]([Cl:1])([Cl:19])[P:11](=[O:12])([O-:18])[O-:15])(=[O:7])[O-:10])[CH3:6]

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 2785333CLODRONIC ACID,TETRAETHYL ESTERHCID 131718818HCID 131718818, compound

Product 1

HCID 15786045HCID 15786045, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

5.0 g (0.014 moles) of tetraethyl (dichloromethylene)bisphosphonate and 6.7 g (0.045 moles) of NaI are dissolved in 50 ml of anhydrous CH3CN and while stirring 12.2 g (0.112 moles) of trimethylsilyl chloride are added. After the addition stirring is continued at room temperature, protected from moisture, for appr. 4 days and is evaporated under a vacuum. To the mixture obtained as a residue (contains as the major component monoethyl tris(trimethylsilyl) (dichloromethylene)bisphosphonate) 10 ml of water are added and the mixture is made alkaline with a 10% NaOH solution. The mixture is diluted with 50 ml of CH3OH and is left standing at +4° C. for 2 h and is filtered (the precipitate is (dichloromethylene)bisphosphonic acid sodium salt). To the filtrate 25 ml of ethanol are added and it is left standing for 1 day at +4° C. and is filtered. The filtrate is evaporated under a vacuum and the residue is washed with acetone and filtered. The precipitate is dried to constant weight whereby appr. 2.0 g (50% of the theor.) of colourless crystalline (dichloromethylene)bisphosphonic acid monoethyl ester trisodium salt are obtained (31P-NMR (D2O): δ 6 11.86 (P), 9.40 (P') 2JPP =15.4 Hz) at a concentration of >90% and wherefrom the corresponding acid may be liberated with acid treatment.

Workup

  1. additionare added
  2. additionAfter the addition
  3. customis continued at room temperature
  4. custom4 days and is evaporated under a vacuum
  5. customTo the mixture obtained as a residue (
  6. additionare added
  7. waitis left
  8. filtrationis filtered (the precipitate
  9. additionTo the filtrate 25 ml of ethanol are added
  10. waitit is left
  11. waitstanding for 1 day at +4° C.
  12. filtrationis filtered
  13. customThe filtrate is evaporated under a vacuum
  14. washthe residue is washed with acetone
  15. filtrationfiltered
  16. customThe precipitate is dried to constant weight whereby appr

Sources & evidence

ORD record
ord-75de7d753d9f45a2b55e56bc1fc861f8
Source dataset
uspto-grants-1994_12
Patent number
US05376649

Reaction notes

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