Methylamine → N,3-Dimethylbenzenesulfonamide

HRID 2077513Notes

Reaction equation

HRID 2077513 reaction equation
[CH3:1][NH2:2].[C:3]1([CH3:13])[CH:8]=[CH:7][CH:6]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:4]=1>C(O)C.CCOC(C)=O.O>[CH3:1][NH:2][S:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH3:13])[CH:4]=1)(=[O:11])=[O:10]

Participants

6

Reactant 2

HCID 6329MethylamineHCID 27345953-Methylbenzenesulphonyl chloride

Product 1

HCID 16789325N,3-DimethylbenzenesulfonamideYield 98%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A RBF was charged with methylamine (0.9 mL, 40%, 28 mmol) in ethanol (2 mL). The mixture was chilled to 0° C. in an ice bath while stirred under an inert atmosphere. Then, m-toluenesulfonyl chloride (0.8 mL, 6 mmol) was added dropwise into the mixture. The resulting mixture was allowed to stir at 0° C. under an inert atmosphere for 30 minutes. The mixture was diluted with EtOAc and water and then the aqueous layer was extracted three times with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give N,3-dimethylbenzenesulfonamide (1.0 g, 98% yield) as a colorless oil. MS (ESI pos. ion) m/z: 173 (MH+). Calculated exact mass for C7H10NO2S: 172.

Workup

  1. stirringto stir at 0° C. under an inert atmosphere for 30 minutes
  2. extractionthe aqueous layer was extracted three times with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-315dabb2ac32451e85b6cfdc9774af24
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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