p-Toluenesulfonic acid → N-[2-[4-[6-chloro-2-ethyl-5-(trifluoromethyl)benzimidazol-1-yl]phenyl]ethyl]-N-(4-methylphenyl)sulfonylcarbamate;4-methylbenzenesulfonic acid

HRID 858474Notes

Reaction equation

HRID 858474 reaction equation
[Cl:1][C:2]1[C:3]([C:35]([F:38])([F:37])[F:36])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:33]=[CH:32][C:15]([CH2:16][CH2:17][N:18]([S:22]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=4)(=[O:24])=[O:23])[C:19](=[O:21])[O-:20])=[CH:14][CH:13]=3)[C:6]=2[CH:34]=1.[C:39]1([CH3:49])[CH:44]=[CH:43][C:42]([S:45]([OH:48])(=[O:47])=[O:46])=[CH:41][CH:40]=1>CC(C)=O>[Cl:1][C:2]1[C:3]([C:35]([F:38])([F:37])[F:36])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:33]=[CH:32][C:15]([CH2:16][CH2:17][N:18]([S:22]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=4)(=[O:23])=[O:24])[C:19](=[O:20])[O-:21])=[CH:14][CH:13]=3)[C:6]=2[CH:34]=1.[CH3:49][C:39]1[CH:44]=[CH:43][C:42]([S:45]([OH:48])(=[O:47])=[O:46])=[CH:41][CH:40]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 17963428HCID 17963428, compound

Product 1

HCID 86585627N-[2-[4-[6-chloro-2-ethyl-5-(trifluoromethyl)benzimidazol-1-yl]phenyl]ethyl]-N-(4-methylphenyl)sulfonylcarbamate;4-methylbenzenesulfonic acidYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(6-chloro-2-ethyl-5-trifluoromethyl-1H-benzimidazol-1-yl)phenethyl(4-methylphenyl)sulfonylcarbamate (Example 106, 150 mg, 0.265 mmol), p-toluenesulfonic acid (50.5 mg, 0.265 mmol) in acetone (3% H2O, 0.3 ml) was stirred at room temperature for 16 h. The precipitated crystalline solids were filtered, washed with acetone (0.05 ml×5), and dried in vacuo at 40° C. for 2 h to afford 158 mg (81%) of the title compound as white solids.

Workup

  1. filtrationThe precipitated crystalline solids were filtered
  2. washwashed with acetone (0.05 ml×5)
  3. customdried in vacuo at 40° C. for 2 h

Sources & evidence

ORD record
ord-7f772bca7abc4b309f307991f7f5dbbd
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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