Benzenesulfonic Acid → Clopidogrel Besylate

HRID 1671499Notes

Reaction equation

HRID 1671499 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)CCCCCCCCC>[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 81741-DecanolSolvent

Procedure

Clopidogrel base (10 g) was dissolved in decan-1-ol at 50-55° C. To this, benzene sulfonic acid (5 g) was added at 50-55° C. and the reaction mixture was stirred for about 20 hr. The solid was filtered and washed with methyl tertiary butyl ether and dried in 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 methyl tertiary butyl ether
  3. customdried in vacuum oven for at least 20 hr

Sources & evidence

ORD record
ord-fe1c7728c2e14b57850f91882d516f4b
Source dataset
uspto-grants-2011_08
Patent number
US07994322B2

Reaction notes

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