p-Toluenesulfonic acid → HCID 14800481, compound

HRID 704327Notes

Reaction equation

HRID 704327 reaction equation
[C:1]([NH:4][C:5]1[CH:33]=[CH:32][CH:31]=[CH:30][C:6]=1[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)(=O)[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:2][C:1]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][S:23]([C:26]([F:29])([F:27])[F:28])(=[O:24])=[O:25])=[CH:20][CH:21]=3)=[CH:11][CH:10]=2)[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14800480HCID 14800480, compound

Product 1

HCID 14800481HCID 14800481, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-acetylamino-N-[4-(4-trifluoromethylsulfonyloxyphenoxy)benzyl]aniline (500 mg), p-toluenesulfonic acid (50 mg) and toluene (50 ml) was heated under reflux while removing the by-produced water therefrom through a Dean-Stark trap. After the by-production of water ceased, the reaction mixture was cooled to room temperature, washed with a saturated sodium carbonate solution and water in order and distilled under reduced pressure to eliminate toluene. The residue was purified by silica gel column chromatography to give 2-methyl-1-[4-(4-trifluoromethylsulfonyloxyphenoxy)benzyl]benzimidazole (433 mg) as a colorless oil. nD25.0 1.5670.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customwhile removing the by-produced water
  4. washwashed with a saturated sodium carbonate solution and water in order
  5. distillationdistilled under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2bdda0d8cb084d48957cd3904ce1855f
Source dataset
uspto-grants-1991_01
Patent number
US04987145

Reaction notes

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