Sodium Cyanide → N-(p-toluenesulfonyl)-3-(bromomethyl)4-(cyanomethyl)-3-pyrroline

HRID 1534646Notes

Reaction equation

HRID 1534646 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][C:13]([CH2:15][Br:16])=[C:12]([CH2:17]Br)[CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C-:20]#[N:21].[Na+]>CS(C)=O>[C:1]1([CH3:19])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:11][C:12]([CH2:17][C:20]#[N:21])=[C:13]([CH2:15][Br:16])[CH2:14]2)(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 199082361-p-Toluenesulfonyl-3,4-bis(bromomethyl)-3-pyrroline

Product 1

HCID 19908246N-(p-toluenesulfonyl)-3-(bromomethyl)4-(cyanomethyl)-3-pyrrolineYield 57.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10 g of N-(p-toluenesulfonyl)-3,4-bis(bromomethyl)-3-pyrroline, prepared in Preparation 5, was dissolved in 10 ml of dimethylsulfoxide (DMSO) and then heated in oil bath for 2 hours with refluxing. During the heating and refluxing, 1.5 g of sodium cyanide was added by small portion. The reaction mixture was cooled to room temperature and poured into ice water and then extracted with methylene chloride (200 ml×3). The extracts were combined, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography. 5 g of the title compound was obtained (yield 57%).

Workup

  1. temperatureheated in oil bath for 2 hours
  2. temperaturewith refluxing
  3. temperatureDuring the heating and refluxing
  4. extractionextracted with methylene chloride (200 ml×3)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b05fc246bca4c47bd7154b80a9e899d
Source dataset
uspto-grants-1992_02
Patent number
US05089621

Reaction notes

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