Sulfuric Acid → Clopidogrel bisulfate

HRID 887996Notes

Reaction equation

HRID 887996 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[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[Cl:12])=[O:4].[OH:25][S:22]([OH:26])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 60606Clopidogrel

Product 1

HCID 115366Clopidogrel bisulfate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
7.5 °C

Procedure

Clopidogrel (10 g) obtained from example 3 was dissolved in acetone (43 ml) at 5-10° C. and concentrated sulfuric acid (1.78 ml) was added dropwise in 10 minutes at 5-10° C. The resulting solution was stirred for 1 hour at 5-10° C. The resulting solid was filtered and dried under reduced pressure at 50° C. for 5 hours.

Workup

  1. filtrationThe resulting solid was filtered
  2. customdried under reduced pressure at 50° C. for 5 hours

Sources & evidence

ORD record
ord-ccba87dc7b294d239191be6ffb69c4b6
Source dataset
uspto-grants-2012_08
Patent number
US08247558B2

Reaction notes

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