Sulfuric Acid → Clopidogrel bisulfate

HRID 1015683Notes

Reaction equation

HRID 1015683 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:18][C:17]2[CH:19]=[CH:20][S:21][C:16]=2[CH2:15][CH2:14]1)[C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[S:22](=[O:26])(=[O:25])([OH:24])[OH:23]>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:18][C:17]2[CH:19]=[CH:20][S:21][C:16]=2[CH2:15][CH2:14]1)[C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[OH:25][S:22]([OH:26])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 1118Sulfuric Acid2×HCID 60606Clopidogrel

Product 1

HCID 115366Clopidogrel bisulfate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

S (+) clopidogrel, 90 gm was dissolved in ethyl acetate (1.0 Liter). It was stirred and sulfuric acid 30 gm was added at room temperature. After complete addition of sulfuric acid, the reaction mixture was heated at reflux for 1 hour. It was then cooled and further stirred at room temperature for 1 hour. The product so obtained was filtered under vacuum at 60-70° C. for 6-8 hours.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperatureIt was then cooled
  4. stirringfurther stirred at room temperature for 1 hour
  5. customThe product so obtained
  6. filtrationwas filtered under vacuum at 60-70° C. for 6-8 hours

Sources & evidence

ORD record
ord-c9dda14bf951460b87b4f8ef44accf90
Source dataset
uspto-grants-2011_07
Patent number
US07985859B2

Reaction notes

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