Diethanolamine → 4-acetyl-N,N-bis(2-hydroxyethyl)benzenesulfonamide

HRID 866970Notes

Reaction equation

HRID 866970 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+].[OH:28][CH2:29][CH2:30][NH:31][CH2:32][CH2:33][OH:34]>O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:31]([CH2:32][CH2:33][OH:34])[CH2:30][CH2:29][OH:28])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 2664184-Acetylbenzenesulfonyl chlorideHCID 23668814Sodium 4-acetylbenzenesulphonate

Product 1

HCID 227502694-acetyl-N,N-bis(2-hydroxyethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The damp 4-acetylbenzenesulfonyl chloride from 300 g. of sodium 4-acetylbenzenesulfonate is added in portions to a well-stirred, cooled solution of 500 ml. of bis(2-hydroxyethyl)amine in 750 ml. of water. The mixture is stirred at room temperature for 16 hours, cooled to 0°-5° C. and the precipitate of 4-acetyl-N,N-bis(2-hydroxyethyl)benzenesulfonamide is collected by filtration and crystallized from water; m.p. 87.5°-89.5° C.

Workup

  1. temperaturecooled solution of 500 ml
  2. temperaturecooled to 0°-5° C.
  3. filtrationthe precipitate of 4-acetyl-N,N-bis(2-hydroxyethyl)benzenesulfonamide is collected by filtration
  4. customcrystallized from water

Sources & evidence

ORD record
ord-881d0b5deaf14b76a5897d567062c9f2
Source dataset
uspto-grants-1978_07
Patent number
US04101661

Reaction notes

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