Hydrochloric Acid → 4-(Methylsulfonyl)aniline
Reaction equation
[OH2:1].[CH3:2][S:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[OH:11]O.Cl>C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:2][S:3]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)(=[O:11])=[O:1]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
67 mg of Na2WO4, 8 drops of acetic acid and 19 mL of H2O were placed in a flask and the mixture was heated to 65° C. 19 mL (153 mmol) of 4-methylthioaniline was added followed by 34.5 mL (337 mmol) of H2O2 dropwise. The mixture was stirred at 65° C. for 1.5 h and, after cooling, 800 mL of 1N HCl and 500 mL of CHCl3 was added. The layers were separated and the aqueous phase was washed with more CHCl3. The aqueous phase was basified with 25% NaOH and extracted with CHCl3. The organic phase was washed with brine and dried over MgSO4. The solvent was removed, yielding the product as a white solid (19.80 g, 75%).
Workup
- temperatureafter cooling
- customThe layers were separated
- washthe aqueous phase was washed with more CHCl3
- extractionextracted with CHCl3
- washThe organic phase was washed with brine
- dry with materialdried over MgSO4
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-75a33162cf344c79b7da587791f9724a
- Source dataset
- uspto-grants-2005_01
- Patent number
- US06838476B1
Reaction notes
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