P-Toluenesulfonamide → 1-p-Toluenesulfonyl-3,4-bis(bromomethyl)-3-pyrroline

HRID 1534810Notes

Reaction equation

HRID 1534810 reaction equation
[Br:1][CH2:2][C:3]([CH2:9]Br)=[C:4]([CH2:7][Br:8])[CH2:5]Br.[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:12]1([CH3:11])[CH:13]=[CH:14][C:15]([S:18]([N:21]2[CH2:9][C:3]([CH2:2][Br:1])=[C:4]([CH2:7][Br:8])[CH2:5]2)(=[O:19])=[O:20])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 11430Potassium CarbonateHCID 353431,4-Dibromo-2,3-bis(bromomethyl)-2-butene

Product 1

HCID 199082361-p-Toluenesulfonyl-3,4-bis(bromomethyl)-3-pyrrolineYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19 g of tetrakis (bromomethyl)ethylene and 9 g of p-toluene sulfonamide were disolved in 220 ml of dimethylformamide. 30 g of anhydrous potassium carbonate was added and then stirred at room temperature for 20 hours. Thereafter solvent was removed by vacuum distillation. 50 ml of ethylacetate was added to obtain solid product, and solid product was purified by silica gel column chromatography. 12 g of the title compound was obtained (yield 60%).

Workup

  1. customThereafter solvent was removed by vacuum distillation
  2. addition50 ml of ethylacetate was added
  3. customto obtain solid product, and solid product
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4ed46a61fa3a499c87d4a2e46e2a8af7
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

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