Dimethylamine → N,N-dimethyl-2-nitrobenzenesulfonamide

HRID 1041249Notes

Reaction equation

HRID 1041249 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].[CH3:20][NH:21][CH3:22]>O1CCOCC1.O1CCCC1>[CH3:20][N:21]([CH3:22])[S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 10340Sodium CarbonateHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 745198N,N-dimethyl-2-nitrobenzenesulfonamideYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-nitro-benzenesulfonyl chloride (15 g, 0.068 mol) in 1,4-dioxane (100 mL) was added sodium carbonate (10.76 g, 0.1015 mol) and 2.000 M of dimethylamine in tetrahydrofuran (40.61 mL) at room temperature and the reaction mixture was stirred for 4 hours. The reaction mixture was partitioned between water and dichloromethane, and the aqueous layer was extracted once with dichloromethane. The combined organic extracts were dried (MgSO4), concentrated, and the solid residue was recrystallized from MeOH to afford N,N-dimethyl-2-nitro-benzenesulfonamide (14.7 g, 94%) as a white solid. LC/MS (ESI+): 230.92 (M+H).

Workup

  1. customThe reaction mixture was partitioned between water and dichloromethane
  2. extractionthe aqueous layer was extracted once with dichloromethane
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customthe solid residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-29875d16a4034c52a3f8951ce2412c40
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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