Aluminum(III) Chloride → 1239768-83-2

HRID 1913895Notes

Reaction equation

HRID 1913895 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][C:8]=1[CH3:15])=[O:5].[Cl-].[Al+3].[Cl-].[Cl-]>CCCCCCC.C(Cl)(Cl)Cl>[OH:13][C:10]1[CH:11]=[C:12]2[C:7](=[C:8]([CH3:15])[CH:9]=1)[NH:6][C:4](=[O:5])[CH2:3][CH2:2]2

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 171269343-Chloro-N-(4-methoxy-2-methylphenyl)propanamide

Product 1

HCID 666816541239768-83-2Yield 42.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8900HeptaneSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 3-chloro-N-(4-methoxy-2-methylphenyl)propaneamide (0.50 g, synthesized from 3-chlorobutyryl chloride and 4-methoxy-2-methylaniline) and aluminum chloride (1.4 g) in n-heptane (4.0 mL) was stirred at 110° C. for 4 days. The reaction mixture was diluted with chloroform, followed by addition of ice-cold water under ice cooling. After stirring at room temperature for 1 hour, the organic layer and the aqueous layer were separated. The aqueous layer was extracted with ethyl acetate, and the organic layers were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform/methanol=10/0 to 97/3) to give the titled compound (0.166 g, 39%) as a light-brown solid.

Workup

  1. additionfollowed by addition of ice-cold water under ice cooling
  2. stirringAfter stirring at room temperature for 1 hour
  3. customthe organic layer and the aqueous layer were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform/methanol=10/0 to 97/3)

Sources & evidence

ORD record
ord-cf0da3ed1b7f49408c509085dec0093d
Source dataset
uspto-grants-2013_12
Patent number
US08609847B2

Reaction notes

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