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P-Toluenesulfonamide → 2,5-Ditosyl-1,2,3,4,5,6-hexahydropyrrolo[3,4-c]pyrrole

HRID 1534643
Notes
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Reaction equation

HRID 1534643 reaction equation
Br[CH2:2][C:3]([CH2:9]Br)=[C:4]([CH2:7]Br)[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.[H-].[Na+]>CN(C)C=O>[C:12]1([CH3:11])[CH:13]=[CH:14][C:15]([S:18]([N:21]2[CH2:7][C:4]3[CH2:5][N:21]([S:18]([C:15]4[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][CH:14]=4)(=[O:19])=[O:20])[CH2:9][C:3]=3[CH2:2]2)(=[O:20])=[O:19])=[CH:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 24758Sodium hydrideHCID 353431,4-Dibromo-2,3-bis(bromomethyl)-2-butene

Product 1

HCID 151922522,5-Ditosyl-1,2,3,4,5,6-hexahydropyrrolo[3,4-c]pyrroleYield 54.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30 g of tetrakis (bromomethyl)ethylene and 30 g of p-toluene sulfonamide were dissolved in 400 ml of dimethylformamide. 150 g of potassium carbonate anhydride (or 50% sodium hydride 17 g) was added and then stirred at room temperature for 24 hours. Thereafter, this reaction mixture was distilled under vacuum to remove solvents. By adding 30 ml of water and 100 ml of ethylacetate, 17 g of the title compound was obtained as pale yellow powder (yield 50%).

Workup

  1. distillationThereafter, this reaction mixture was distilled under vacuum
  2. customto remove solvents
  3. additionBy adding 30 ml of water and 100 ml of ethylacetate

Sources & evidence

ORD record
ord-f03b5ab59fc34e3d83f05a355149e801
Source dataset
uspto-grants-1992_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05089621

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes