Docusate → Silver Docusate

HRID 2403135Notes

Reaction equation

HRID 2403135 reaction equation
[N+]([O-])([O-])=O.[Ag+:5].[Na].[CH3:7][CH2:8][CH2:9][CH2:10][CH:11]([CH2:14][O:15][C:16]([CH2:18][CH:19]([S:31]([OH:34])(=[O:33])=[O:32])[C:20]([O:22][CH2:23][CH:24]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:25][CH3:26])=[O:21])=[O:17])[CH2:12][CH3:13].CCCCC(COC(CC(S(O)(=O)=O)C(OCC(CCCC)CC)=O)=O)CC>O>[Ag:5].[CH3:7][CH2:8][CH2:9][CH2:10][CH:11]([CH2:14][O:15][C:16]([CH2:18][CH:19]([S:31]([OH:34])(=[O:33])=[O:32])[C:20]([O:22][CH2:23][CH:24]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:25][CH3:26])=[O:21])=[O:17])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 11339DocusateHCID 24470Silver NitrateHCID 9955175Sodium docusate2×

Product 1

HCID 86612078Silver Docusate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a reaction vessel charged with a magnetic stirbar and protected from light, 5.0 g (29 mmol) of silver nitrate was dissolved in approximately 100 mL of deionized water. To the stirred solution was added, is small portions, 13.1 g (29 mmol) of sodium docusate. As the docusate was added, the solution became gradually gelatinous with attendant difficulties in stirring that were remedied by gently heating the solution. After addition of the final portion of sodium docusate, the warmed solution/suspension was stirred overnight, after which point it was rotary evaporated to yield a slightly tan mass. The mass was extracted with a chloroform-acetonitrile mixture, into which much of the material dissolved but some white solid (presumed to be NaNO3) did not. The mixture was filtered and evaporated under reduced pressure to give a soft mass of slightly off-white final product (which should be stored away from light because it is photosensitive). This material was soluble in lidocaine docusate, some organic solvents, and was relatively slow to dissolve in water, doing so to only a limited degree. The two ions have known antimicrobial and emollient properties, respectively.

Workup

  1. additionIn a reaction vessel charged with a magnetic stirbar
  2. additionTo the stirred solution was added
  3. temperatureby gently heating the solution
  4. stirringthe warmed solution/suspension was stirred overnight
  5. customafter which point it was rotary evaporated
  6. customto yield a slightly tan mass
  7. extractionThe mass was extracted with a chloroform-acetonitrile mixture, into which much of the material
  8. dissolutiondissolved
  9. filtrationThe mixture was filtered
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4e34847c3f1841c9a561041011907785
Source dataset
uspto-grants-2014_08
Patent number
US08802596B2

Reaction notes

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