Water → Warfarin Potassium

HRID 1636003Notes

Reaction equation

HRID 1636003 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-].[K+:28].[K+].O>CC(O)C>[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].[K+:28]

Participants

5

Reactant 3

HCID 962Water2×HCID 11430Potassium Carbonate2×HCID 54678486Warfarin2×

Product 1

HCID 23706212Warfarin Potassium

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Warfarin potassium salt is prepared by refluxing the pure warfarin acid with an equivalent amount or an excess of potassium carbonate in 2-propanol. The 2-propanol may be anhydrous or may contain about 0.5% to about 10% water, preferably about 1% to about 3% water. The molar ratio of potassium carbonate to warfarin acid is between about 0.9 and about 2, and is preferably between about 1.0 and about 1.3. The reaction may be conducted at a temperature ranging from room temperature to the boiling point of the solvent for a time of from about 1 hour to about 5 hours. Preferably, the reaction is conducted at reflux temperature and the preferred reaction time is from about 2 hours to about 3 hours. The unreacted carbonate is removed by filtration. The warfarin potassium is precipitated and isolated as a pure crystalline solid by filtration and drying.

Workup

  1. customThe reaction
  2. customranging from room temperature to the boiling point of the solvent for a time of from about 1 hour to about 5 hours
  3. temperatureat reflux temperature
  4. waitthe preferred reaction time is from about 2 hours to about 3 hours
  5. customThe unreacted carbonate is removed by filtration
  6. customThe warfarin potassium is precipitated
  7. customisolated as a pure crystalline solid by filtration
  8. customdrying

Sources & evidence

ORD record
ord-7e7d3f8b9c28412caa6c1752c8bf10cb
Source dataset
uspto-grants-2003_01
Patent number
US06512005B2

Reaction notes

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