Benzenesulfonic Acid → Clopidogrel Besylate

HRID 1671500Notes

Reaction equation

HRID 1671500 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].[C:22]1([S:28]([OH:31])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(C)C>[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].[CH:25]1[CH:26]=[CH:27][C:22]([S:28]([OH:31])(=[O:30])=[O:29])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 60606Clopidogrel

Product 1

HCID 9847991Clopidogrel Besylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Clopidogrel base (60 g) was dissolved in isopropanol at 50-55° C. To it was added benzene sulfonic acid (30 g) dissolved in isopropanol at 50-55° C. The reaction mixture was stirred for 20 hr. The solid was filtered and washed with isopropanol and dried in a vacuum oven for at least 20 hr. to give Clopidogrel besylate, which on characterization was found to be crystalline form, M.P. 130-135° C.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with isopropanol
  3. customdried in a vacuum oven for at least 20 hr

Sources & evidence

ORD record
ord-09ce9ef5291e4bb18d51a8e7f372bae5
Source dataset
uspto-grants-2011_08
Patent number
US07994322B2

Reaction notes

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