Aluminum(III) Chloride → HCID 14268518, compound

HRID 1913894Notes

Reaction equation

HRID 1913894 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]=1F)=[O:5].[Cl-:16].[Al+3].[Cl-].[Cl-]>CCCCCCC.C(Cl)(Cl)Cl>[Cl:16][C:12]1[CH:11]=[C:10]([OH:13])[CH:9]=[C:8]2[C:7]=1[NH:6][C:4](=[O:5])[CH2:3][CH2:2]2

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 66684152HCID 66684152, compound

Product 1

HCID 14268518HCID 14268518, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8900HeptaneSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 3-chloro-N-(2-fluoro-4-methoxyphenyl)propaneamide (1.0 g, synthesized from 3-chlorobutyryl chloride and 2-fluoro-4-methoxyaniline) and aluminum chloride (5.0 g) in n-heptane (2.0 mL) was stirred at 110° C. for 3 days. The reaction mixture was diluted with chloroform, followed by addition of ice-cold water under ice cooling. After stirring at room temperature for 2 hours, the organic layer and the aqueous layer were separated. The aqueous layer was extracted with chloroform, 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: hexane/ethyl acetate=3/2) and NH-type silica gel column chromatography (eluting solvent: chloroform/methanol=99/1 to 9/1) to give the titled compound (0.059 g, 7%) as a light-yellow solid.

Workup

  1. additionfollowed by addition of ice-cold water under ice cooling
  2. stirringAfter stirring at room temperature for 2 hours
  3. customthe organic layer and the aqueous layer were separated
  4. extractionThe aqueous layer was extracted with chloroform
  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: hexane/ethyl acetate=3/2) and NH-type silica gel column chromatography (eluting solvent: chloroform/methanol=99/1 to 9/1)

Sources & evidence

ORD record
ord-e08ac1ec9eb7402bba4d5869b40170e1
Source dataset
uspto-grants-2013_12
Patent number
US08609847B2

Reaction notes

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