Ethanol → N,3-Dimethylbenzenesulfonamide
Reaction equation
[CH3:1][NH2:2].C(O)C.[C:6]1([CH3:16])[CH:11]=[CH:10][CH:9]=[C:8]([S:12](Cl)(=[O:14])=[O:13])[CH:7]=1>>[CH3:1][NH:2][S:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH3:16])[CH:7]=1)(=[O:14])=[O:13]Participants
Procedure
A round-bottom flask with methylamine solution 40% (0.9 ml, 28 mmol) in ethanol (2 ml, 34 mmol), was chilled to 0° C. in an ice bath with stirring under inert atmosphere. Then m-toluenesulfonyl chloride (0.8 ml, 6 mmol) was added slowly into the mixture. The mixture was allowed to stir at 0° C., while under inert atmosphere for 30 minutes. The progress of the reaction was monitored by LC/MS, which showed mostly desired product peak. The mixture was diluted with ethyl acetate and water and then extracted the organic layer with EtOAc (3×25 ml) and brine solution. The organics were combined, dried over sodium sulfate, filtered and concentrated in vacuo. This gave N,3-dimethylbenzenesulfonamide (1.00 g, 98% yield) as a colorless oil. MS (ESI pos. ion) m/z: 186 (MH+). Calc'd exact mass for C8H11NO2S: 185. 1H NMR (400 MHz, chloroform-d): 2.35-2.46 (m, 3H), 2.64 (s, 3H), 4.91 (s, 1H), 7.36-7.46 (m, 2H), 7.64-7.73 (m, 2H).
Workup
- stirringto stir at 0° C., while under inert atmosphere for 30 minutes
Sources & evidence
- ORD record
- ord-c602d263247647828ef431205291583d
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928140B2
Reaction notes
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