p-Toluenesulfonic acid monohydrate → HCID 86682358, compound

HRID 2283606Notes

Reaction equation

HRID 2283606 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.[Cl:13][C:14]1[C:15]([O:30][C:31]2[CH:36]=[C:35]([F:37])[C:34]([C:38]([F:41])([F:40])[F:39])=[CH:33][C:32]=2[C:42]2[CH:47]=[CH:46][N:45]=[N:44][CH:43]=2)=[CH:16][C:17]([F:29])=[C:18]([S:20]([NH:23][C:24]2[N:25]=[CH:26][S:27][CH:28]=2)(=[O:22])=[O:21])[CH:19]=1>CC(C)=O>[CH3:12][C:2]1[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[Cl:13][C:14]1[C:15]([O:30][C:31]2[CH:36]=[C:35]([F:37])[C:34]([C:38]([F:39])([F:40])[F:41])=[CH:33][C:32]=2[C:42]2[CH:47]=[CH:46][N:45]=[N:44][CH:43]=2)=[CH:16][C:17]([F:29])=[C:18]([S:20]([NH:23][C:24]2[N:25]=[CH:26][S:27][CH:28]=2)(=[O:22])=[O:21])[CH:19]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 56598617HCID 56598617, compound

Product 1

HCID 86682358HCID 86682358, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of p-toluenesulfonic acid monohydrate (0.851 g, 4.41 mmol) in acetone (10 mL) was added to a solution of 5-chloro-2-fluoro-4-[5-fluoro-2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,3-thiazol-4-ylbenzenesulfonamide (2.42 g, 4.41 mmol) in acetone (15 mL). After stirring at ambient temperature for 15 minutes, the reaction mixture was concentrated in vacuo. The residue was suspended in diethyl ether (75 mL) and stirred for 2 hours. The resulting solid was collected by filtration, dried, and then recrystallized from ethyl acetate-heptane-methanol (20:10:1) to afford the title compound as a tan crystalline solid (1.78 g, 56%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. stirringstirred for 2 hours
  3. filtrationThe resulting solid was collected by filtration
  4. customdried
  5. customrecrystallized from ethyl acetate-heptane-methanol (20:10:1)

Sources & evidence

ORD record
ord-8f06b163062d4143b5e1e0df3f1eee12
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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