2,6-Dimethylaniline → HCID 20524768, compound

HRID 1702741Notes

Reaction equation

HRID 1702741 reaction equation
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2][CH3:3].[CH3:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:10]=1[NH2:11]>C1(C)C=CC=CC=1>[CH3:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:10]=1[NH:11][S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5]

Participants

4

Reactant 2

HCID 68962,6-DimethylanilineHCID 662791-Propanesulfonyl chloride

Product 1

HCID 20524768HCID 20524768, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1-propanesulphonyl chloride (25 ml) in toluene (50 ml) was added during 15 minutes to a stirred solution of 2,6-dimethylaniline (55 ml) in toluene (400 ml). The mixture was stirred and boiled under reflux for 20 hours, then cooled and filtered. The toluene solution was washed with dilute hydrochloric acid (3 times) and water, then extracted (3 times) with dilute sodium hydroxide solution. The aqueous alkaline solution was acidified with dilute hydrochloric acid, and the product collected by filtration, washed with water and dried. Crystallisation from toluene/60°-80° petrol gave 2',6'-dimethyl-1-propanesulphonanilide as buff coloured crystals (28.0 g, 55%), melting point 72°.

Workup

  1. temperatureunder reflux for 20 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe toluene solution was washed with dilute hydrochloric acid (3 times) and water
  5. extractionextracted (3 times) with dilute sodium hydroxide solution
  6. filtrationthe product collected by filtration
  7. washwashed with water
  8. customdried
  9. customCrystallisation from toluene/60°-80° petrol

Sources & evidence

ORD record
ord-59841ee4fc8341928e99292259ff7743
Source dataset
uspto-grants-1982_09
Patent number
US04349378

Reaction notes

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