N,N-Dimethylethylenediamine → 4-acetyl-N-(2-dimethylaminoethyl)benzenesulfonamide

HRID 866981Notes

Reaction equation

HRID 866981 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(C1C=CC(S([O-])(=O)=O)=CC=1)(=O)C.[Na+].[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][NH2:32]>O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:32][CH2:31][CH2:30][N:29]([CH3:33])[CH3:28])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 2664184-Acetylbenzenesulfonyl chlorideHCID 23668814Sodium 4-acetylbenzenesulphonate

Product 1

HCID 80361544-acetyl-N-(2-dimethylaminoethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The damp 4-acetylbenzenesulfonyl chloride from 100 g. of sodium 4-acetylbenzenesulfonate is added to a solution of 83 g. of N,N-dimethylethylenediamine in 730 ml. of water. The mixture is stirred at room temperature for 16 hours, cooled, and the precipitate of 4-acetyl-N-(2-dimethylaminoethyl)benzenesulfonamide collected by filtration, washed with water and dried; m.p. 87°-89° C. after crystallization from 2-propanol/hexane.

Workup

  1. temperaturecooled
  2. filtrationthe precipitate of 4-acetyl-N-(2-dimethylaminoethyl)benzenesulfonamide collected by filtration
  3. washwashed with water
  4. customdried
  5. customm.p. 87°-89° C. after crystallization from 2-propanol/hexane

Sources & evidence

ORD record
ord-f392ac5e43e8406d93fa49e749bf50e0
Source dataset
uspto-grants-1978_07
Patent number
US04101661

Reaction notes

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