Dimethyl Sulfoxide → 3',5'-Dimethoxy-4'-(methylamino)-2-(methylsulfonyl)-acetophenone
Reaction equation
[CH3:1][S:2]([CH3:5])(=[O:4])=[O:3].[H-].[Na+].CS(C)=O.C[O:13][C:14](=O)[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([NH:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1>C(O)(=O)C.O>[CH3:26][O:25][C:17]1[CH:16]=[C:15]([C:14](=[O:13])[CH2:1][S:2]([CH3:5])(=[O:4])=[O:3])[CH:20]=[C:19]([O:21][CH3:22])[C:18]=1[NH:23][CH3:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A suspension of 44.2 g. of dimethylsulfone and 16 g. of sodium hydride (50% dispersion in oil) in 150 ml. of absolute dimethylsulfoxide was stirred at 50° C. for 4 hours under an atmosphere of nitrogen and the exclusion of moisture. 30.4 g. of 3,5-dimethoxy-4-(methylamino)-benzoic acid methyl ester were added and the mixture was stirred at 80° C. for 10 minutes and at 25° C. for 30 minutes. The mixture was then dissolved in 600 ml. of water and the solution was made neutral by the addition of glacial acetic acid. The precipitate was removed by filtration with suction, washed with water, dried and recrystallized from ethyl acetate, whereby there was obtained 3',5'-dimethoxy-4'-(methylamino)-2-(methylsulfonyl)-acetophenone having a melting point of 98°-99° C.
Workup
- additionA suspension of 44.2 g
- dissolutionThe mixture was then dissolved in 600 ml
- customThe precipitate was removed by filtration with suction
- washwashed with water
- customdried
- customrecrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-a19f3dccb5e9408da80e230d89e55bf5
- Source dataset
- uspto-grants-1988_12
- Patent number
- US04792557
Reaction notes
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