Acetic Acid → HCID 14800488, compound

HRID 704329Notes

Reaction equation

HRID 704329 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[C:3]=1[NH2:4].[C:32](O)(=O)[CH3:33]>>[Cl:1][C:2]1[C:3]2[N:4]=[C:32]([CH3:33])[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][S:25]([C:28]([F:30])([F:29])[F:31])(=[O:27])=[O:26])=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 15107249HCID 15107249, compound

Product 1

HCID 14800488HCID 14800488, compound

Procedure

A mixture of 2-chloro-6-[4-(4-trifluoromethylsulfonyloxyphenoxy)benzylamino]aniline (300 mg) and acetic acid (5 ml) was heated under reflux for 6 hours. The reaction mixture was cooled to room temperature, excessive acetic acid was removed by distillation under reduced pressure, and toluene (100 ml) and a 5% sodium hydroxide solution (50 ml) were added thereto, followed by stirring for 10 minutes. The toluene layer was separated, washed with water, dried over anhydrous sodium sulfate and distilled under reduced pressure to eliminate toluene The residue was purified by silica gel column chromatography to give 4-chloro-2-methyl-1-[4-(4-trifluoromethylsulfonyloxyphenoxy)benzyl]benzimidazole (285 mg) as a colorless liquid. nD24 1.5655.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customexcessive acetic acid was removed by distillation under reduced pressure, and toluene (100 ml)
  4. additiona 5% sodium hydroxide solution (50 ml) were added
  5. customThe toluene layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d25d5224ad584407b141b092d57f8ca6
Source dataset
uspto-grants-1991_01
Patent number
US04987145

Reaction notes

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