Sulfuric Acid → Clopidogrel bisulfate

HRID 1792111Notes

Reaction equation

HRID 1792111 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:21][C:17]2[CH:18]=[CH:19][S:20][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[Cl:12])=[O:4].[S:22](=[O:26])(=[O:25])([OH:24])[OH:23]>CC(C)=O>[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:21][C:17]2[CH:18]=[CH:19][S:20][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 AcidHCID 60606Clopidogrel

Product 1

HCID 115366Clopidogrel bisulfateYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Clopidogrel base (3.42 g) was dissolved in acetone (27 mL). Aqueous sulfuric acid (20%, 4.57 mL) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. The solution was cooled to room temperature and stirred at this temperature for additional 1.5 hours. Then the solvent was evaporated to dryness under reduced pressure to obtain powder (3.59 g, 78%) which characterization data showed to be the amorphous form.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature for 2 hours
  3. customThen the solvent was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b576c48cd9f74a05ae8ae061f693d5bb
Source dataset
uspto-grants-2006_07
Patent number
US07074928B2

Reaction notes

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