2-Methoxyethylamine → 3-Bromo-n-(2-methoxyethyl)benzenesulfonamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:12][O:13][CH2:14][CH2:15][NH2:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:16][CH2:15][CH2:14][O:13][CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 3-bromobenzenesulfonyl chloride (1.00 g, 3.72 mmol) in acetone (10 mL) was added 2-methoxyethylamine (0.97 mL, 11.15 mmol, 3.0 eq) and potassium carbonate (2.57 g, 18.6 mmol, 5.0 eq), and the reaction was stirred at 40° C. for 5 h. The mixture was cooled to room temperature and then partitioned between EtOAc and water, and the organic phase was washed with brine, dried over MgSO4, and concentrated at reduced pressure. The residue was purified by MPLC (20% to 25% EtOAc/hexane) to give 1.05 g (96%) of the desired product as an oil. TLC [30% EtOAc/hexane], Rf=0.33.
Workup
- temperatureThe mixture was cooled to room temperature
- custompartitioned between EtOAc and water
- washthe organic phase was washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated at reduced pressure
- customThe residue was purified by MPLC (20% to 25% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-c96d4e9e91e44908a7bf78c940c12a25
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207166B2
Reaction notes
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