Dimethylamine → N,N-Dimethyl 3-nitrobenzenesulfonamide

HRID 1633918

Reaction equation

HRID 1633918 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:14][NH:15][CH3:16]>C1COCC1>[CH3:14][N:15]([CH3:16])[S:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 84763-Nitrobenzenesulfonyl chloride

Product 1

HCID 224495N,N-Dimethyl 3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Nitrobenzenesulfonyl chloride (22.8 mmol, 5.05 g) was dissolved in dry THF (50 mL). Dimethylamine in THF (2M, 34 mL) was added and the mixture was refluxed for 2 hours. Upon cooling, the mixture was filtered and the filtrate was evaporated in vacuo. The residue was dissolved in ethyl acetate (250 mL), washed with water (3×50 mL) and dried over MgSO4. Evaporation of the solvent afforded the title compound.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureUpon cooling
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate (250 mL)
  6. washwashed with water (3×50 mL)
  7. dry with materialdried over MgSO4
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3371dc23fafb4b658677b97423ae6551
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Linked notes

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