Aluminum(III) Chloride → HCID 10734538, compound

HRID 1031664Notes

Reaction equation

HRID 1031664 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[C:11]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][C:9]([C:19]([CH3:21])=[O:20])=[C:8]([O:22]C)[CH:7]=1)(=[O:4])=[O:3].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[OH:22][C:8]1[CH:7]=[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:11]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][C:9]=1[C:19]([CH3:21])=[O:20]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 14722293N-(4-Acetyl-5-methoxy-2-phenoxyphenyl)methanesulfonamide

Product 1

HCID 10734538HCID 10734538, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.0 g of methyl 4-methylsulfonylamino-2-methoxy-5-phenoxyphenyl ketone was dissolved in 100 ml of methylene chloride. 3.98 g of aluminum chloride was added thereto in portions in 30 minutes with ice-cooling. The mixture was stirred for 1 hour at 20°-25° C. The reaction mixture was introduced into 100 ml of ice water. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting crystal was recrystallized from isopropyl alcohol to obtain 8.8 g (yield: 91.9%) of methyl 2-hydroxy-4-methylsulfonylamino-5-phenoxyphenyl ketone having a melting point of 151-153° C.

Workup

  1. temperaturein portions in 30 minutes with ice-cooling
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe resulting crystal was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-9b687fb1db874433a5940b75e8602764
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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