p-Toluenesulfonic acid monohydrate → p-Toluenesulfonate

HRID 1517484Notes

Reaction equation

HRID 1517484 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.O.[C:51]1([CH3:61])[CH:56]=[CH:55][C:54]([S:57]([OH:60])(=[O:59])=[O:58])=[CH:53][CH:52]=1>C(O)CCC>[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.[S:57]([C:54]1[CH:55]=[CH:56][C:51]([CH3:61])=[CH:52][CH:53]=1)([O-:60])(=[O:59])=[O:58]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 468616221240425-05-1

Product 2

HCID 85570p-ToluenesulfonateYield 73%HCID 468616221240425-05-1

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

To compound (I) (3 g, 1.0 mol eq, limiting reagent) was charged butan-1-ol (135 mL, 45 rel vol). The temperature was adjusted to 100° C. and a solution formed. p-Toluenesulfonic acid monohydrate (1.06 g, 1.0 mol eq) was dissolved in butan-1-ol (12 mL, 4 rel vol). This solution was charged to the reaction. A butan-1-ol line rinse (3 mL, 1 rel vol) was charged. Following stirring, temperature cycling and cooling, the solid was isolated by filtration, washed twice with butan-1-ol (2×4.5 mL, 2×1.5 rel vol) and dried to constant weight yielding compound (I) tosylate (2.96 g, 4.03 mmol, 73%).

Workup

  1. customwas adjusted to 100° C.
  2. customa solution formed
  3. additionThis solution was charged to the reaction
  4. washA butan-1-ol line rinse (3 mL, 1 rel vol)
  5. additionwas charged
  6. temperaturetemperature cycling and cooling
  7. customthe solid was isolated by filtration
  8. washwashed twice with butan-1-ol (2×4.5 mL, 2×1.5 rel vol)
  9. customdried to constant weight

Sources & evidence

ORD record
ord-e36d2e87f2e1477599f6318adf545f6d
Source dataset
uspto-grants-2012_07
Patent number
US08232296B2

Reaction notes

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