Aluminum(III) Chloride → HCID 9841844, compound

HRID 430476Notes

Reaction equation

HRID 430476 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH2:5]([N:9]([CH3:30])[C:10](=[O:29])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18](=[O:28])[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[O:26]C)[CH:12]=1)[CH2:6][CH2:7][CH3:8]>C(Cl)Cl>[CH2:5]([N:9]([CH3:30])[C:10](=[O:29])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18](=[O:28])[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[OH:26])[CH:12]=1)[CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 15549731HCID 15549731, compound

Product 1

HCID 9841844HCID 9841844, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

AlCl3 (307 mg, 2.30 mmol) was added to a solution of N-butyl-N-methyl-3-{(4-chloro-2-methoxybenzoyl)amino}benzamide (345 mg, 0.92 mmol) in CH2Cl2 (3.7 mL) at 25°. The mixture was kept at 25° for 17 h. The mixture then was partitioned between EtOAc (75 mL) and aqueous 1 N HCl (50 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (10-40μ silica gel, EtOAc:hexane, 1:1) to give the title compound (272 mg, 82% yield) as a white foam:

Workup

  1. customThe mixture then was partitioned between EtOAc (75 mL) and aqueous 1 N HCl (50 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (10-40μ silica gel, EtOAc:hexane, 1:1)

Sources & evidence

ORD record
ord-abedf3120cdb43d1bdc6e9432cb57ddd
Source dataset
uspto-grants-2001_11
Patent number
US06323202B1

Reaction notes

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