Dimethylamine → N,N-dimethyl-4-nitrobenzenesulfonamide

HRID 1247104Notes

Reaction equation

HRID 1247104 reaction equation
[CH3:1][NH:2][CH3:3].[N+:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1)([O-:6])=[O:5]>CO>[CH3:1][N:2]([CH3:3])[S:13]([C:10]1[CH:9]=[CH:8][C:7]([N+:4]([O-:6])=[O:5])=[CH:12][CH:11]=1)(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 2747580N,N-dimethyl-4-nitrobenzenesulfonamideYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of dimethylamine (180 mL, 40% in water, 1.57 mol) in methanol (180 mL) at 0° C., was slowly added 4-nitrobenzenesulfonyl chloride (69.5 g, 314 mmol). After complete addition, the cold bath was removed; and, after stirring overnight, the mixture was filtered and the precipitate was washed with water and dried in vacuo to give 68 g (94%) of tan solid.

Workup

  1. customat 0° C.
  2. additionAfter complete addition
  3. customthe cold bath was removed
  4. filtrationthe mixture was filtered
  5. washthe precipitate was washed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e0df8e8081dc4131a00b8f0792881392
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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