Dimethylamine → N,N-dimethyl-1-(3-nitrophenyl)methanesulfonamide

HRID 1890975Notes

Reaction equation

HRID 1890975 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][S:11](Cl)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:15][NH:16][CH3:17]>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][S:11]([N:16]([CH3:17])[CH3:15])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 13196775(3-Nitrophenyl)methanesulfonyl chloride

Product 1

HCID 28632733N,N-dimethyl-1-(3-nitrophenyl)methanesulfonamideYield 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(3-Nitrophenyl)methanesulfonyl chloride (2.36 g, 10 mmol) was dissolved in benzene (30 mL), then to this solution was added 40% aqueous dimethylamine (12.6 mL, 0.1 mol) and the reaction mixture was vigorously stirred for 2 h at room temperature. The benzene layer was separated and the aqueous layer extracted with CH2Cl2 (2×25 mL). The recombined organic layers were washed with saturated aqueous NaHCO3 (30 mL), water (30 mL) and the solvent removed under reduced pressure to give 2.32 g (95%) of (3-nitrophenyl)-N,N-dimethylmethanesulfonamide as crystals.

Workup

  1. customThe benzene layer was separated
  2. extractionthe aqueous layer extracted with CH2Cl2 (2×25 mL)
  3. washThe recombined organic layers were washed with saturated aqueous NaHCO3 (30 mL), water (30 mL)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7efed34bf5134ffaa876b362094f85d0
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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