p-Toluenesulfonic acid → HCID 178464090, compound

HRID 1620535Notes

Reaction equation

HRID 1620535 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:13]2/[C:14]([NH:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[N:15][C:16](=[O:18])[S:17]/2)[CH2:8][CH2:7]1.[S:40]([C:44]1[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=1)([OH:43])(=[O:42])=[O:41]>C(O)C>[S:40]([C:44]1[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=1)([OH:43])(=[O:42])=[O:41].[S:40]([C:44]1[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=1)([OH:43])(=[O:42])=[O:41].[F:39][C:2]([F:1])([F:38])[C:3]1[CH:33]=[C:32]([C:34]([F:36])([F:37])[F:35])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:13]2/[C:14]([NH:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][N:25]([CH2:26][CH3:27])[CH2:28][CH3:29])=[N:15][C:16](=[O:18])[S:17]/2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 178464089HCID 178464089, compound

Product 1

HCID 178464090HCID 178464090, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of (5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]piperidin-4-yl}methylidene)-4-({2-[2-(diethylamino)ethoxy]ethyl}amino)-1,3-thiazol-2(5H)-one (950 mg) in ethanol (2 mL) was added a solution of tosylic acid (635 mg) in ethanol (3 mL). The reaction mixture was stirred at room temperature for 1 hr, and the solvent was evaporated under reduced pressure. The residue was recrystallized from 2-butanone/heptane to give the title compound (992 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was recrystallized from 2-butanone/heptane

Sources & evidence

ORD record
ord-9a1f415af64749f1b0748e25f4046a25
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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