Hydrochloric Acid → N-(2,6-dimethylphenyl)-4-methylbenzenesulfonamide

HRID 484783Notes

Reaction equation

HRID 484783 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.Cl>N1C=CC=CC=1>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([NH:4][C:3]2[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=2[CH3:1])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68962,6-DimethylanilineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 262999N-(2,6-dimethylphenyl)-4-methylbenzenesulfonamideYield 136.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 23.4 g (0.12 mole) of 2,6-dimethylaniline and 40.5 g (0.19 mole) of p-toluenesulfonyl chloride in 75 ml of pyridine was heated at reflux for three hours. The mixture was cooled and poured into vigorously stirred 2N hydrochloric acid. The crude product was recrystallized from ethanol to give 45 g of the title compound. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Workup

  1. temperatureat reflux for three hours
  2. temperatureThe mixture was cooled
  3. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-795c7189b36c44c7b08a9d3db755d75c
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

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