Potassium thiocyanate → 1-(alpha-Thiocyanoacetyl) azetidine

HRID 1973635Notes

Reaction equation

HRID 1973635 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:8][CH2:7][CH2:6]1)=[O:4].[S-:9][C:10]#[N:11].[K+]>C(O)C>[S:9]([CH2:2][C:3]([N:5]1[CH2:8][CH2:7][CH2:6]1)=[O:4])[C:10]#[N:11]

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 25431591-(Azetidin-1-yl)-2-chloroethan-1-one

Product 1

HCID 536707741-(alpha-Thiocyanoacetyl) azetidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(α-Chloroacetyl) azetidine (13 grams; 0.1 mol), potassium thiocyanate (18 grams; 0.18 mol) and ethanol (100 ml) are charged into a glass reaction flask equipped with stirrer and reflux condenser. The reaction mixture is then heated at reflux, with stirring, for a period of about 4 hours. After this time the reaction mixture is cooled and filtered. The filtrate is then stripped of ethanol leaving a residue. The residue is extracted twice with hot benzene and the two benzene extracts are combined. The benzene extract is then evaporated under reduced pressure to yield 1-(α-thiocyanoacetyl) azetidine as a residue.

Workup

  1. customequipped with stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture is then heated
  4. temperatureat reflux
  5. temperatureAfter this time the reaction mixture is cooled
  6. filtrationfiltered
  7. extractionThe residue is extracted twice with hot benzene
  8. extractionThe benzene extract
  9. customis then evaporated under reduced pressure

Sources & evidence

ORD record
ord-d16fa4394c0e450db58adfab8008724e
Source dataset
uspto-grants-1976_12
Patent number
US03998808

Reaction notes

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