Sodium Hydroxide → HCID 86748346, compound

HRID 1492891Notes

Reaction equation

HRID 1492891 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH:13]([P:22](=[O:29])([O:26]CC)[O:23]CC)[P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+:31]>C(O)C>[Na+:31].[C:1]1([S:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH:13]([P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])[P:22](=[O:23])([OH:29])[O-:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9934281HCID 9934281, compound

Product 1

HCID 86748346HCID 86748346, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of tetraethyl 4-(phenylthio)butylaminomethylenebisphosphonate (2.5 g) in ethanol (20 ml) was added a solution of sodium hydroxide (450 mg) in ethanol (20 ml). The mixture was heated under reflux for 4 hours and concentrated under reduced pressure. The residue was dissolved in water and the solution was subjected to column chromatography on Amberlite CG-50 (H+ form) and eluted with water to obtain diethyl 4-(phenylthio)butylaminomethylenebisphosphonate monosodium salt (810 mg). The resultant was recrystallized from methanol-hexane, m.p. 143°-145° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. washeluted with water

Sources & evidence

ORD record
ord-e0f10f2f87f745a0965fb111cbeec4cf
Source dataset
uspto-grants-1994_12
Patent number
US05376647

Reaction notes

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