Potassium Carbonate → N-allyl-N-alpha-methylbenzyl-4-hydroxybenzenesulfonamide

HRID 358425Notes

Reaction equation

HRID 358425 reaction equation
[CH2:1]([NH:4][CH:5]([CH3:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].C([O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)(=O)C1C=CC=CC=1>CC(C)=O>[CH2:1]([N:4]([CH:5]([CH3:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[S:34]([C:31]1[CH:32]=[CH:33][C:28]([OH:27])=[CH:29][CH:30]=1)(=[O:36])=[O:35])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 190100Benzenesulfonyl chloride, 4-(benzoyloxy)-HCID 2793834(1-Phenylethyl)(prop-2-EN-1-YL)amine

Product 1

HCID 187212N-allyl-N-alpha-methylbenzyl-4-hydroxybenzenesulfonamideYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 1.61 g (0.01 mol) of N-allyl-N-α-methylbenzylamine and 1.38 g of potassium carbonate in 15 ml of acetone was dropped a solution of 2.62 g (0.084 mol) of 4-benzoyloxybenzenesulfonyl chloride in 5 ml of acetone under ice-cooling conditions. The mixture was subjected to the reaction at room temperature for 30 minutes and then at 50° C. for 1 hour. After completion of the reaction, the inorganic salt was removed by filtration and the acetone was distilled off, then, the contents were admixed with 150 ml of a 20% potassium hydroxide solution in ethanol, followed by refluxing for 30 minutes. After completion of the reaction, the reaction mixture was poured into ice-water to permit crystals to precipitate. The crystals were washed with a dilute acidic solution and a dilute alkaline solution, followed by sufficiently washing with water, drying in vacuum and recrystallizing from a mixed solvent of benzene and n-hexane to obtain 2.00 g of N-allyl-N-α-methylbenzyl-4-hydroxybenzenesulfonamide (melting point 128° to 129° C.).

Workup

  1. temperaturecooling conditions
  2. customThe mixture was subjected to the reaction at room temperature for 30 minutes
  3. customAfter completion of the reaction
  4. customthe inorganic salt was removed by filtration
  5. distillationthe acetone was distilled off
  6. temperatureby refluxing for 30 minutes
  7. customAfter completion of the reaction
  8. customto precipitate
  9. washThe crystals were washed with a dilute acidic solution
  10. washby sufficiently washing with water
  11. customdrying in vacuum
  12. customrecrystallizing from a mixed solvent of benzene and n-hexane

Sources & evidence

ORD record
ord-b7cfe68a2627465f89365b0030191c4b
Source dataset
uspto-grants-1984_08
Patent number
US04468245

Reaction notes

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