Iodoethane → HCID 20068980, Verbindung

HRID 982016

Reaktionsgleichung

Reaktionsgleichung von HRID 982016
[Na].[C:2]([CH2:4][C:5](=O)[CH3:6])#[N:3].[H-].[Na+].Cl[CH2:11][C:12](=[O:14])[CH3:13].[OH-].[Na+].[CH2:17](I)[CH3:18].[C:20](=[S:22])=[S:21]>CN(C)C=O>[CH2:17]([S:22][C:20]1[S:21][C:11]([C:12](=[O:14])[CH3:13])=[C:5]([CH3:6])[C:4]=1[C:2]#[N:3])[CH3:18]

Komponenten

9

Edukt 7

HCID 6340IodoethaneHCID 6348Carbon DisulfideHCID 6571ChloroacetoneHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 755793-OxobutyronitrileHCID 5360545Sodium

Produkt 1

HCID 20068980HCID 20068980, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 10.5 g of sodium salt of cyanoacetone in 200 ml of dimethylformamide 9.0 ml of carbon disulphide are gradually added while stirring cooling in ice and keeping under nitrogen, succeeded by 4.5 g of sodium hydride dispersion. After stirring for an hour with cooling, 8.4 ml of chloroacetone are added dropwise under the same reaction conditions. After stirring for another hour, 0.4 g of powdered NaOH are added and finally, after again stirring for another 0.5 hour, 8.0 ml of ethyl iodide under the same conditions. After stirring, the reaction mixture for again another hour and leaving to stand overnight it is poured 1 l of ice water and extracted with diethyl ether. The organic phase is washed with water three times, dried, treated with charcoal, filtered and evaporated. After recrystallisation from isopropanol, the residue yields the desired product in a yield of 9.54 g; melting-point 51°-52° C.

Aufarbeitung

  1. additionare gradually added
  2. temperaturecooling in ice
  3. stirringAfter stirring for an hour
  4. temperaturewith cooling
  5. stirringAfter stirring for another hour
  6. stirringfinally, after again stirring for another 0.5 hour
  7. stirringAfter stirring
  8. waitthe reaction mixture for again another hour
  9. customleaving
  10. extractionextracted with diethyl ether
  11. washThe organic phase is washed with water three times
  12. customdried
  13. additiontreated with charcoal
  14. filtrationfiltered
  15. customevaporated
  16. customAfter recrystallisation from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-5ca4d5a75a124d0a8296a3c6089d58fd
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04994485

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