Acetyl chloride → N-(4-Acetyl-5-methoxy-2-phenoxyphenyl)methanesulfonamide
Reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([O:19][CH3:20])[CH:9]=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:4])=[O:3].[C:21](Cl)(=[O:23])[CH3:22].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[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:21]([CH3:22])=[O:23])=[C:8]([O:19][CH3:20])[CH:7]=1)(=[O:4])=[O:3]Participants
Procedure
In 100 ml of anhydrous methylene chloride were dissolved 10 g of 3-methylsulfonylamino-4-phenoxyanisole and 2.81 g of acetyl chloride. Thereto was added 9.1 g of aluminum chloride in 5 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 resulting 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 residue was recrystallized from isopropyl alcohol to obtain 9.83 g (yield: 86%) of methyl 4-methylsulfonylamino-2-methoxy-5-phenoxyphenyl ketone having a melting point of 108.5-110° C.
Workup
- temperaturecooling
- customThe resulting organic layer was separated
- washwashed with water
- dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
- customThe solvent was removed by distillation under reduced pressure
- customThe residue was recrystallized from isopropyl alcohol
Sources & evidence
- ORD record
- ord-02b5f74f4b244e99b34c69f82750439e
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04954518
Reaction notes
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