Ethanol → HCID 54306529, compound

HRID 1973627Notes

Reaction equation

HRID 1973627 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[S-:10][C:11]#[N:12].[K+].C(O)C>CCCCC>[S:10]([CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4])[C:11]#[N:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 884401-(Chloroacetyl)pyrrolidineHCID 516872Potassium thiocyanate

Product 1

HCID 54306529HCID 54306529, compound

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

1-(α-Chloroacetyl pyrrolidine (14.7 grams; 0.1 mol), potassium thiocyanate (18 grams; 0.2 mol) and ethanol (50 ml) were charged into a glass reaction flask equipped with a mechanical stirrer and reflux condenser. The reaction mixture was heated at reflux, with stirring, for a period of about 4 hours. The mixture was then cooled and filtered. The filtrate was stripped of solvent to yield a solid product. The solid was extracted with three 200 ml portions of boiling benzene, and the benzene extracts were combined and evaporated under reduced pressure to yield an oil. The oil was poured into pentane wherein it solidified. The solid was recrystallized from a benzene-pentane mixture to yield 1-(α-thiocyanoacetyl) pyrrolidine having a melting point of 95° to 96° C. and having the following elemental analysis; calculated for C7H10N2OS.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux
  5. temperatureThe mixture was then cooled
  6. filtrationfiltered
  7. customto yield a solid product
  8. extractionThe solid was extracted with three 200 ml portions of boiling benzene
  9. customevaporated under reduced pressure
  10. customto yield an oil
  11. customThe solid was recrystallized from a benzene-pentane mixture

Sources & evidence

ORD record
ord-e2d520103c0348c1b979183eb8c229f6
Source dataset
uspto-grants-1976_12
Patent number
US03998808

Reaction notes

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