Aluminum(III) Chloride → HCID 57952160, compound

HRID 603354Notes

Reaction equation

HRID 603354 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([C:18](=[O:21])[CH2:19]Cl)[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=1.[Cl-].[Cl-].[Cl-].[Al+3]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[C:10]2[C:15](=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)[CH2:19][C:18]1=[O:21]

Participants

3

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 57952149HCID 57952149, compound

Product 1

HCID 57952160HCID 57952160, compound

Conditions

Temperature
100 °C

Procedure

In a flask are mixed N-(2′-chloro-6′-methylphenyl)-N-chloroacetyl-4-ethylaniline (2.08 g) are mixed with aluminum trichloride (1.16 g) and the mixture is flushed with nitrogen. The flask is introduced into an oil bath (155-160° C.) and the mixture is stirred under a stream of nitrogen for 4.5 hours. The mixture is slightly cooled to about 100° C., treated with toluene (30 ml) and 1N HCl (20 ml) and stirred for 30 minutes while the temperature decreases gradually. After phase separation, the organic phase is washed with 1N HCl and water, dried (magnesium sulfate) and evaporated. The residue is chromatographed on silica (86 g) using toluene containing 5-20% isopropyl acetate as eluent affording the title product.

Workup

  1. customthe mixture is flushed with nitrogen
  2. additionThe flask is introduced into an oil bath (155-160° C.)
  3. additiontreated with toluene (30 ml) and 1N HCl (20 ml)
  4. stirringstirred for 30 minutes while the temperature
  5. customAfter phase separation
  6. washthe organic phase is washed with 1N HCl and water
  7. dry with materialdried (magnesium sulfate)
  8. customevaporated
  9. customThe residue is chromatographed on silica (86 g)

Sources & evidence

ORD record
ord-282f40f493b248bdb2971cf3c0eb334e
Source dataset
uspto-grants-2011_03
Patent number
US07906677B2

Reaction notes

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