Dimethylamine → N,N-Dimethyl 3-nitrobenzenesulfonamide

HRID 1814645

Reaction equation

HRID 1814645 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-89cc37bfb4614153853c214b9f65ea8c
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Linked notes

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