Pyridine → 1-Cyano-1-methylethyl chloroformate

HRID 1248253

Reaktionsgleichung

Reaktionsgleichung von HRID 1248253
[C:1](Cl)([Cl:3])=[O:2].[CH3:5][C:6]([CH3:10])([OH:9])[C:7]#[N:8].N1C=CC=CC=1.C(=O)=O.CC(O)C>CCOCC>[Cl:3][C:1]([O:9][C:6]([C:7]#[N:8])([CH3:10])[CH3:5])=[O:2]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6371Phosgene2×HCID 6406Acetone CyanohydrinHCID 86586944Isopropanol carbon dioxide

Produkt 1

HCID 53254801-Cyano-1-methylethyl chloroformateAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Into a one liter round bottom flask equipped with a phosgene inlet tube, a dry ice cooled condenser, a Teflon blade stirrer and a dropping funnel were added 200 milliliters (ml) of anhydrous ether. The flask was cooled in a dry ice/2-propanol bath and 100 ml of liquid phosgene (1.5 moles) were introduced. A mixture of acetone cyanohydrin (85 grams, 1 mole) and pyridine (80 ml, 1 mole) in 400 ml of anhydrous ether was added dropwise to the pool of phosgene, through the dropping funnel. When the addition was completed, the dry ice/2-propanol bath was replaced by an ice bath and stirring was continued for two hours. The reaction mixture was then stirred at room temperature for an additional two hours. Nitrogen was introduced into the reactor through the reactor inlet tube to remove the excess phosgene. The phosgene containing nitrogen gas stream removed from the reactor was forwarded to a packed column into the top of which was sprayed a solution of 15 weight percent sodium hydroxide and 0.8 weight percent pyridine. After degassing, the reaction mixture was filtered and dried over anhydrous magnesium sulfate. The ether solvent was evaporated and 123 grams (72% yield) of 1-cyano-1-methylethyl chloroformate as a light yellow liquid was obtained. Identification of the product as 1-cyano-1-methylethylchloroformate was confirmed by infrared and nuclear magnetic resonance (NMR) spectroscopy.

Aufarbeitung

  1. customInto a one liter round bottom flask equipped with a phosgene inlet tube, a dry ice cooled condenser, a Teflon blade stirrer and a dropping funnel
  2. temperatureThe flask was cooled in a dry ice/2-propanol bath
  3. additionWhen the addition
  4. stirringThe reaction mixture was then stirred at room temperature for an additional two hours
  5. additionNitrogen was introduced into the reactor through the reactor inlet tube
  6. customto remove the excess phosgene
  7. additionThe phosgene containing nitrogen gas stream
  8. customremoved from the reactor
  9. customAfter degassing
  10. filtrationthe reaction mixture was filtered
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe ether solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-23a6f7b6e42a475b9f049efaa3b6cf3f
Quelldatensatz
uspto-grants-1985_06
Patentnummer
US04522991

Verknüpfte Notizen

Wird geladen…