p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 37330Notes

Reaction equation

HRID 37330 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The apparatus used in Example 1 was cleaned and charged with 95.1 g (0.50 mol) p-toluenesulfonic acid monohydrate and 750 mL toluene. The mixture was stirred to aid dissolution. MPP (88.13 g, 0.50 mol) was added slowly over 2 min. The reaction reached 38° C. The slurry was stirred for 1.5 hours, filtered, and the white solids allowed to air dry until partially dry (173.6 g). The solids were recrystallized from THF (approx. 1 L), filtered and dried. Dry weight=1782.1 g. Analysis by 1H NMR and FTIR verified the structure as that of the p-toluenesulfonic acid salt of MPP; mp=149°-150° C.; NaOH titration=108.83%; FW=348.48.g/mol; soluble in H2O, MeOH. DMSO and acetone. Calculated for C18H24N2O3S: C, 62.4%; H, 6.94%; N, 8.04%; S, 9.20%; O, 13.77%; Found: C, 62.075; H, 6.90%; N, 7.98%; S, 9.04%; O, 14.01%.

Workup

  1. dissolutiondissolution
  2. additionMPP (88.13 g, 0.50 mol) was added slowly over 2 min
  3. customreached 38° C
  4. stirringThe slurry was stirred for 1.5 hours
  5. filtrationfiltered
  6. customto air dry
  7. customuntil partially dry (173.6 g)
  8. customThe solids were recrystallized from THF (approx. 1 L)
  9. filtrationfiltered
  10. customdried
  11. customDry weight=1782.1 g

Sources & evidence

ORD record
ord-a060a70403824befaf8cb4dbe960adfa
Source dataset
uspto-grants-1995_05
Patent number
US05420223

Reaction notes

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