p-Toluenesulfonic acid monohydrate → p-Toluenesulfonate

HRID 1517480Notes

Reaction equation

HRID 1517480 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(#N)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 85%HCID 468616221240425-05-1

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent2×

Procedure

To compound (I) (3 g, 1.0 mol eq, limiting reagent) was charged butyronitrile (45 mL, 15 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 butyronitrile (18 mL, 6 rel vol). This solution was charged to the reaction. Following stirring and cooling, the solid was isolated by filtration, washed with butyronitrile (4.5 mL, 1.5 rel vol) and dried to constant weight yielding the compound (I) tosylate (3.37 g, 4.70 mmol, 85%).

Workup

  1. customwas adjusted to 100° C.
  2. customa solution formed
  3. additionThis solution was charged to the reaction
  4. temperaturecooling
  5. customthe solid was isolated by filtration
  6. washwashed with butyronitrile (4.5 mL, 1.5 rel vol)
  7. customdried to constant weight

Sources & evidence

ORD record
ord-8d9b94a51e384975b92a080c8bcf2a94
Source dataset
uspto-grants-2012_07
Patent number
US08232296B2

Reaction notes

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