Acetic Acid → HCID 13730387, compound

HRID 978041Notes

Reaction equation

HRID 978041 reaction equation
[CH2:1]([O:3][C:4]1[CH:26]=[CH:25][C:7]([O:8][C:9]2[CH:24]=[CH:23][C:12]([CH2:13][NH:14][C:15]3[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:16]=3[NH2:17])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)[CH3:2].[C:27](O)(=O)[CH3:28]>>[CH3:27][C:28]1[N:14]([CH2:13][C:12]2[CH:23]=[CH:24][C:9]([O:8][C:7]3[CH:25]=[CH:26][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=3)=[CH:10][CH:11]=2)[C:15]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 13883959HCID 13883959, compound

Product 1

HCID 13730387HCID 13730387, compound

Procedure

A mixture of 2-[4-(4-ethoxyphenoxy)benzylamino)-3-methylaniline (0.348 g) and acetic acid (5 ml) was heated under reflux for 6 hours and then cooled to room temperature. Excess 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 remove toluene. The residue was purified by silica gel column chromatography to give 2,7-dimethyl-1-[4-(4-ethoxyphenoxy)benzyl]benzimidazole (0.315 g) as white crystals. m.p., 124.1° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customExcess 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. customto remove toluene
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2081747d521f4bf6983a2e5c7fdd4633
Source dataset
uspto-grants-1987_05
Patent number
US04663339

Reaction notes

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