Dimethylcarbamoyl Chloride → N-(2,3-epoxypropyl)-N-alpha-methylbenzyl-4-(N,N-dimethylcarbamoyloxy)-benzenesulfonamide

HRID 358424Notes

Reaction equation

HRID 358424 reaction equation
[O:1]1[CH2:23][CH:2]1[CH2:3][N:4]([CH:15]([CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[H-].[Na+].[Na].[CH3:27][N:28]([CH3:32])[C:29](Cl)=[O:30]>CN(C)C=O>[O:1]1[CH2:23][CH:2]1[CH2:3][N:4]([CH:15]([CH3:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[S:5]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:29](=[O:30])[N:28]([CH3:32])[CH3:27])=[CH:12][CH:13]=1)(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 187624Benzenesulfonamide, 4-hydroxy-N-(2-oxiranylmethyl)-N-(1-phenylethyl)-HCID 5360545Sodium

Product 1

HCID 13239964N-(2,3-epoxypropyl)-N-alpha-methylbenzyl-4-(N,N-dimethylcarbamoyloxy)-benzenesulfonamideYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g (3 mmol) of N-(2,3-epoxypropyl)-N-α-methylbenzyl-4-hydroxybenzenesulfonamide and 180 mg (3.75 mmol) of 50% sodium hydride were added to 15 ml of dry N,N-dimethylformamide, followed by agitating at room temperature for 30 minutes. To the resulting sodium salt was added 400 mg (3.83 mmol) of N,N-dimethylcarbamoyl chloride for reaction at 60° C. for 1 hour. After completion of the reaction, the excess of the solvent and N,N-dimethylcarbamoyl chloride were removed by distillation under reduced pressure. The residue was dissolved in chloroform and sufficiently washed with water and the chloroform solution was dehydrated over anhydrous magnesium sulfate, followed by distilling off the solvent to obtain a crude product. The crude product was purified by the silica gel chromatography to obtain 980 mg of N-(2,3-epoxypropyl)-N-α-methylbenzyl-4-(N,N-dimethylcarbamoyloxy)-benzenesulfonamide (Compound No. 57). The nD26.0 value was found to be 1.5320. The results of the elemental analysis are shown below.

Workup

  1. customfor reaction at 60° C. for 1 hour
  2. customAfter completion of the reaction
  3. customthe excess of the solvent and N,N-dimethylcarbamoyl chloride were removed by distillation under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washsufficiently washed with water
  6. distillationby distilling off the solvent
  7. customto obtain a crude product
  8. customThe crude product was purified by the silica gel chromatography

Sources & evidence

ORD record
ord-75f90181a487495bb5407fe1e3e209f4
Source dataset
uspto-grants-1984_08
Patent number
US04468245

Reaction notes

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