Sodium Iodide → HCID 21490111, compound

HRID 1973629Notes

Reaction equation

HRID 1973629 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH:9]([CH3:10])[CH2:8][CH2:7][CH:6]1[CH3:11])=[O:4].[S-:12][C:13]#[N:14].[K+].[I-].[Na+]>C(O)C>[S:12]([CH2:2][C:3]([N:5]1[CH:9]([CH3:10])[CH2:8][CH2:7][CH:6]1[CH3:11])=[O:4])[C:13]#[N:14]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 516872Potassium thiocyanateHCID 21490114HCID 21490114, compound

Product 1

HCID 21490111HCID 21490111, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(α-Chloroacetyl)-2,5-dimethylpyrrolidine (10 grams; 0.057 mol), potassium thiocyanate (10.1 grams), sodium iodide (a few crystals) and ethanol (100 ml) were charged into a glass reaction flask equipped with mechanical stirrer and reflux condenser. The reaction mixture was heated at reflux, with stirring, for a period of about 2 hours. After this time the reaction mixture was cooled and filtered. The filtrate was stripped of ethanol under reduced pressure resulting in a solid product. The solid was extracted with two 125 ml portions of hot benzene. The benzene extracts were combined and were evaporated to yield 1-(α-thiocyanoacetyl)-2,5-dimethylpyrrolidine as a light brown oil having a refractive index at 25° C. of 1.5185 and having the following elemental analysis as calculated for C9H14N2OS.

Workup

  1. customequipped with mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux
  5. temperatureAfter this time the reaction mixture was cooled
  6. filtrationfiltered
  7. customresulting in a solid product
  8. extractionThe solid was extracted with two 125 ml portions of hot benzene
  9. customwere evaporated

Sources & evidence

ORD record
ord-003864997c464f9593a6b3add12bd8a3
Source dataset
uspto-grants-1976_12
Patent number
US03998808

Reaction notes

Loading…