Acetone → Warfarin Sodium

HRID 1636002Notes

Reaction equation

HRID 1636002 reaction equation
[CH3:1][C:2]([CH2:4][CH:5]([C:12]1[C:21](=[O:22])[O:20][C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]=1[OH:23])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:3].C(=O)([O-])[O-].[Na+:28].[Na+].CC(C)=O.CC(=O)CC>O>[CH3:1][C:2]([CH2:4][CH:5]([C:12]1[C:21](=[O:22])[O:20][C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]=1[O-:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[Na+:28]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6569Methyl Ethyl KetoneHCID 10340Sodium CarbonateHCID 54678486Warfarin

Product 1

HCID 16204922Warfarin Sodium

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Warfarin sodium is prepared by refluxing the pure warfarin acid with an excess of sodium carbonate in a polar solvent such as acetone or butanone, which may be either anhydrous or contain from about 1% to about 10% water. The unreacted sodium carbonate is preferably removed by filtration. The product is isolated by evaporating the solvent to dryness or by precipitating the salt by addition of a nonpolar solvent such as hexane, cyclohexane, heptane and the like, and filtering and drying the precipitate.

Workup

  1. customThe unreacted sodium carbonate is preferably removed by filtration
  2. customThe product is isolated
  3. customby evaporating the solvent to dryness
  4. customby precipitating the salt
  5. additionby addition of a nonpolar solvent such as hexane, cyclohexane, heptane
  6. filtrationthe like, and filtering
  7. customdrying the precipitate

Sources & evidence

ORD record
ord-bd08c8a43fff4b25a4325945e3315297
Source dataset
uspto-grants-2003_01
Patent number
US06512005B2

Reaction notes

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