Ethanol → Naproxen Sodium

HRID 1927635Notes

Reaction equation

HRID 1927635 reaction equation
C(O)C(O)C.[Na].[CH3:7][C@H:8]([C:21]([OH:23])=[O:22])[C:9]1[CH:10]=[CH:11][C:12]2[CH:13]=[C:14]([O:19][CH3:20])[CH:15]=[CH:16][C:17]=2[CH:18]=1.[O-]CC.[Na+:27].C(O)C>C(OCC)C>[CH3:7][C@H:8]([C:21]([O-:23])=[O:22])[C:9]1[CH:10]=[CH:11][C:12]2[CH:13]=[C:14]([O:19][CH3:20])[CH:15]=[CH:16][C:17]=2[CH:18]=1.[Na+:27]

Participants

7

Reactant 5

HCID 702EthanolHCID 1030Propylene Glycol2×HCID 156391Naproxen2×HCID 2723922Sodium ethoxide2×HCID 5360545Sodium

Product 1

HCID 23681059Naproxen Sodium

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A propylene glycol solvate of a sodium salt of naproxen was prepared. To a solution of naproxen (348 mg, 1.51 mmol) in diethyl ether (10 mL) was added propylene glycol (0.200 ml, 2.72 mmol). To the clear solution was added sodium ethoxide in ethanol (21%, 0.750 mL, 2.01 mmol). The solution became slightly yellow due to the sodium ethoxide. After 1 minute, crystals began to form. After 5 minutes, the solid had completely crystallized. The solid was collected by filtration and was washed with diethyl ether (10 mL) The product was then air-dried and collected. The solvate was 2:1 naproxen Na:propylene glycol. The solid was characterized by TGA and PXRD.

Workup

  1. customwas prepared
  2. customto form
  3. waitAfter 5 minutes
  4. customthe solid had completely crystallized
  5. filtrationThe solid was collected by filtration
  6. washwas washed with diethyl ether (10 mL) The product
  7. customwas then air-dried
  8. customcollected

Sources & evidence

ORD record
ord-329321aed1b64048b142f0818da42aa7
Source dataset
uspto-grants-2012_05
Patent number
US08183290B2

Reaction notes

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