Sodium hydride → N-Allyl-N-(alpha-methyl-2-chlorobenzyl)benzenesulfonamide

HRID 224532Notes

Reaction equation

HRID 224532 reaction equation
[CH2:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3].[H-].[Na+].[Na].[CH3:17][CH:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25]>CN(C)C=O>[CH2:1]([N:4]([CH:18]([CH3:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 257467n-AllylbenzenesulfonamideHCID 5870341-Chloro-2-(1-chloroethyl)benzeneHCID 5360545Sodium

Product 1

HCID 23331021N-Allyl-N-(alpha-methyl-2-chlorobenzyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.97 g (0.01 mole) of N-allylbenzenesulfonamide was added to 0.58 g (0.012 mole) of 50% sodium hydride in 15 ml of dry N,N-dimethylformamide. The mixture was stirred at room temperature for 30 minutes to react them. To the resulting sodium salt was added 2.10 g (0.012 mole) of α-methyl-2-chlorobenzyl chloride. The mixture was stirred at room temperature for 1 hour. The N,N-dimethyl formamide was distilled off under reduced pressure, and cold water was added. The resulting oil layer was extracted with benzene. The benzene layer was dried over anhydrous magnesium sulfate, concentrated, and purified by silica gel chromatography to afford the final product. The final product is designated as compound No. 89 in Table 2, and its melting point and elemental analysis values are shown in Table 2.

Workup

  1. customto react them
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. distillationThe N,N-dimethyl formamide was distilled off under reduced pressure, and cold water
  4. additionwas added
  5. extractionThe resulting oil layer was extracted with benzene
  6. dry with materialThe benzene layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e34992c041d64e4f88ecfe12dc444722
Source dataset
uspto-grants-1980_11
Patent number
US04233061

Reaction notes

Loading…