Bromoacetonitrile → O-Ethyl S-cyanomethyl xanathate

HRID 352705Notes

Reaction equation

HRID 352705 reaction equation
Br[CH2:2][C:3]#[N:4].[C:5](=[S:10])([O:7][CH2:8][CH3:9])[S-:6].[K+]>C(O)C.O>[O:7]([CH2:8][CH3:9])[C:5]([S:10][CH2:2][C:3]#[N:4])=[S:6]

Participants

5

Reactant 2

HCID 11534BromoacetonitrileHCID 2735045Potassium ethylxanthate

Product 1

HCID 162885O-Ethyl S-cyanomethyl xanathateYield 90.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of bromoacetonitrile (12.4 g) and potassium O-ethyl dithiocarbonate (16.0 g) in ethanol (200 mL) were allowed to stir at room temperature for 16 hours. The reaction was diluted with water (100 mL) and the organics extracted with diethyl ether. The combined organic layers were washed twice with water, then brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue purified by column chromatography (silica-gel 60, 70-230 mesh) eluting with 4:6 ethyl acetate:petroleum spirit 40-60° C. to afford the title compound as a yellow oil (14.6 g, 90.7%). 1H-nmr (CDCl3) δ 1.48 (t, 3H); 3.88 (s, 2H); 4.72 (q, 2H). 13C-nmr (CDCl3) δ 13.7, 21.3, 71.5, 115.7, 209.2.

Workup

  1. extractionthe organics extracted with diethyl ether
  2. washThe combined organic layers were washed twice with water
  3. dry with materialbrine and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue purified by column chromatography (silica-gel 60, 70-230 mesh)
  6. washeluting with 4:6 ethyl acetate

Sources & evidence

ORD record
ord-cc70dcf173524cbc82e8e0e74d681ced
Source dataset
uspto-grants-2004_06
Patent number
US06747111B2

Reaction notes

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