Dimethylamine → 2-cyano-N,N-dimethylbenzenesulfonamide

HRID 1822723Notes

Reaction equation

HRID 1822723 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9](Cl)(=[O:11])=[O:10])#[N:2].[CH3:13][NH:14][CH3:15].C(N(CC)CC)C>C(OCC)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([N:14]([CH3:15])[CH3:13])(=[O:11])=[O:10])#[N:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 5223472-Cyanobenzenesulfonyl Chloride

Product 1

HCID 6978732-cyano-N,N-dimethylbenzenesulfonamideYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-cyanobenzensulfonylchloride (2.0 g, 10 mmol), dimethyl amine (1.18 g, 10 mmol, 40 wt % in water) and triethylamine (1.5 mL, 10 mmol) were stirred together at room temperature for 30 min. The resulting slurry was diluted with ethyl acetate and filtered. The filter cake was washed with ethyl acetate and the combined filterate was washed with water, dried (Na2SO4) and concentrated to give the title product as orange plates (1.78 g, 85% yield). 1HNMR (300 MHz, CDCl3) δ: 8.02 (1H, dd, J=8.05, 1.46 Hz), 7.87 (1H, dd, J=7.32, 1.47 Hz), 7.79–7.76 (2H, m), 2.86 (6H, s). LCMS calcd for C9H11N2O2S (M+H): 211.05; found: 211.09.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with ethyl acetate
  3. washthe combined filterate was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-39f0f8406c3449d3a295e48cb0c36258
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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