Aluminum(III) Chloride → HCID 22414877, compound

HRID 1721421Notes

Reaction equation

HRID 1721421 reaction equation
[CH2:1]([N:8]([C:19](=[O:24])[C:20](Br)([CH3:22])[CH3:21])[C:9]1[CH:14]=[C:13]([O:15]CC)[CH:12]=[CH:11][C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1>[CH2:1]([N:8]1[C:9]2[C:14](=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=2[CH3:18])[C:20]([CH3:21])([CH3:22])[C:19]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 22414890HCID 22414890, compound

Product 1

HCID 22414877HCID 22414877, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
125 °C

Procedure

31.2 g (80.0 mmol) of N-benzyl-2-bromo-5'-ethoxy-2'-methylisobutyranilide was dissolved in 258 ml of chlorobenzene. After the addition of 53.2 g (399 mmol) of aluminum chloride powder, the mixture was heated while stirring for 28 minutes at 125° C. The resulting mixture was cooled, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was purified by column chromatography (silica gel, 3:1 mixture of n-hexane and ethyl acetate) and recrystallized (ether-n-hexane) to obtain 9.06 g (yield, 40.3%) of colorless prisms of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe resulting mixture was cooled
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by column chromatography (silica gel, 3:1 mixture of n-hexane and ethyl acetate)
  8. customrecrystallized (ether-n-hexane)
  9. customto obtain

Sources & evidence

ORD record
ord-f66305ac957f448f8925da771c8c434f
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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