Toluene → Clopidogrel Besylate

HRID 555968Notes

Reaction equation

HRID 555968 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.C1(C)C=CC=CC=1>CO>[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

5

Reactant 3

HCID 1140TolueneHCID 7371Benzenesulfonic AcidHCID 60606Clopidogrel

Product 1

HCID 9847991Clopidogrel Besylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Clopidogrel base was dissolved in methanol. Benzene sulphonic acid was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hrs. The solution was cooled to room temperature and the methanolic solution was added drop-wise to the boiling toluene. The resulting solution was refluxed for an additional 20 minutes. The solution was cooled to room temperature and was stirred at this temperature for extended hours. The solvent was evaporated under reduced pressure to dryness to obtain Clopidogrel besylate, similar to that obtained above.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature for 2 hrs
  3. temperatureThe resulting solution was refluxed for an additional 20 minutes
  4. temperatureThe solution was cooled to room temperature
  5. customThe solvent was evaporated under reduced pressure to dryness

Sources & evidence

ORD record
ord-9213157a343a4b0a8f9446985b90d4b1
Source dataset
uspto-grants-2011_11
Patent number
US08053579B2

Reaction notes

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