p-Toluenesulfonic acid → HCID 131715124, compound

HRID 978042Notes

Reaction equation

HRID 978042 reaction equation
[C:1]([NH:4][C:5]1[C:10]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([S:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:27])(=O)[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:27][C:6]1[C:5]2[N:4]=[C:1]([CH3:2])[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([S:19][C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 131715125HCID 131715125, compound

Product 1

HCID 131715124HCID 131715124, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-acetamido-1-chloro-3-[4-(4-methylthiophenoxy)benzylamino]benzene (0.413 g), p-toluenesulfonic acid (0.040 g) and toluene (150 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 and distilled under reduced pressure to remove toluene. The residue was purified by silica gel column chromatography to give 4-chloro-2-methyl-1-[4-(4-methylthiophenoxy)benzyl]benzimidazole (0.375 g) as a colorless liquid. nD22.0 1.6341.

Workup

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

Sources & evidence

ORD record
ord-24b7107f562b4bcaab4c9a282140adc1
Source dataset
uspto-grants-1987_05
Patent number
US04663339

Reaction notes

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