Methylamine → N-Methyl-4-nitrobenzenesulfonamide

HRID 2414799Notes

Reaction equation

HRID 2414799 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][NH2:15]>CCOCC>[CH3:14][NH:15][S:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 232993N-Methyl-4-nitrobenzenesulfonamideYield 98.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 4-nitrobenzenesulfonyl chloride (5 g, 22.56 mmol) in ether (250 ml), methylamine (5 ml, 40% aq. solution, 56.4 mmol) was added, and the mixture was stirred at room temperature. After 16 hr, the reaction mixture was concentrated to remove the solvent and the residue was resuspended in methylene chloride. After washing with 2N HCl and brine, the organic fractions were dried (MgSO4), filtered and concentrated to give N-methyl-4-nitrobenzenesulfonamide (4.8 g, 98%): mp (DSC) 109° C. Anal Calc'd. for C7H8N2O4S: C, 38.89; H, 3.73; N, 12.96. Found: C, 38.83; H, 3.72; N, 12.96.

Workup

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated
  3. customto remove the solvent
  4. washAfter washing with 2N HCl and brine
  5. dry with materialthe organic fractions were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2d4445e8007b4c8997d59c74d8efd1b9
Source dataset
uspto-grants-2004_11
Patent number
US06815460B2

Reaction notes

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