2,5-Dimethylbenzenesulfonic acid → 2,5-Dimethylbenzene-1-sulfonate(1-)

HRID 1517477Notes

Reaction equation

HRID 1517477 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][C:13]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[C:17](=[O:29])[C:16]([C:30]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][N:35]=2)=[O:31])=[CH:15][C:14]=1[C:44]1[N:48]([CH3:49])[N:47]=[CH:46][CH:45]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[C:61]1([CH3:72])[C:62]([S:68]([OH:71])(=[O:70])=[O:69])=[CH:63][C:64]([CH3:67])=[CH:65][CH:66]=1>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH3:12][C:13]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:26])[F:28])[CH:20]=2)[C:17](=[O:29])[C:16]([C:30]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][N:35]=2)=[O:31])=[CH:15][C:14]=1[C:44]1[N:48]([CH3:49])[N:47]=[CH:46][CH:45]=1.[C:61]1([CH3:72])[C:62]([S:68]([O-:71])(=[O:70])=[O:69])=[CH:63][C:64]([CH3:67])=[CH:65][CH:66]=1

Participants

5

Reactant 3

HCID 118682,5-Dimethylbenzenesulfonic acidHCID 85570p-ToluenesulfonateHCID 468616221240425-05-12×

Product 2

HCID 69990162,5-Dimethylbenzene-1-sulfonate(1-)HCID 468616221240425-05-1

Procedure

Compound (I) p-xylene-2-sulfonate was synthesized using an analogous method to that described for the synthesis of compound (I) tosylate in Example 8a from compound (I) (50 mg, 0.092 mmol) and p-xylene-2-sulfonic acid (20 mg, 0.092 mmol). No precipitation was obtained after stirring over night. After the evaporation of 50% of the solvent and stirring for an extra night a good precipitation of the title product was obtained; yield 56 mg, 0.076 mmol, 83%. The compound (I) p-xylene-2-sulfonate (2,5-dimethylbenzenesulfonate) Form A was crystalline and gave the powder X-ray diffraction pattern shown in FIG. 8.

Workup

  1. customCompound (I) p-xylene-2-sulfonate was synthesized
  2. customNo precipitation
  3. customwas obtained
  4. customAfter the evaporation of 50% of the solvent
  5. stirringstirring for an extra night
  6. customa good precipitation of the title product
  7. customwas obtained

Sources & evidence

ORD record
ord-438ce4eb73d84732bca6ebd740833c8e
Source dataset
uspto-grants-2012_07
Patent number
US08232296B2

Reaction notes

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