Aluminum(III) Chloride → HCID 68501471, compound

HRID 1176537Notes

Reaction equation

HRID 1176537 reaction equation
[CH3:1][C:2]([CH3:17])=[CH:3][C:4]([NH:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:5].[Cl-].[Cl-].[Cl-].[Al+3]>ClCCCl.ClCCl>[CH3:1][C:2]1([CH3:17])[C:16]2[C:7](=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:13]=[CH:14][CH:15]=2)[NH:6][C:4](=[O:5])[CH2:3]1

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 19177455HCID 19177455, compound

Product 1

HCID 68501471HCID 68501471, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 15.18 g of methyl 2-(3-methyl-but-2-enoylamino)benzoate and 35.07 g of aluminium trichloride in 250 ml of 1,2-dichloroethane is stirred at reflux over 30 minutes. The reaction mixture is cooled to room temperature, diluted with dichloromethane, washed with 1N HCl (2×) and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a brown solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.21 (3:7 EtOAc-heptane); Rt=3.98.

Workup

  1. temperatureat reflux over 30 minutes
  2. washwashed with 1N HCl (2×) and brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-326754878b1f4b5d8422286798403d11
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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