Sodium Cyanide → Ethyl thiazole-4-carboxylate

HRID 2397211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2397211
[N+:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[C-:2].[CH:9](OCC)=[S:10].[C-]#N.[Na+]>C(O)C>[CH2:7]([O:6][C:4]([C:3]1[N:1]=[CH:2][S:10][CH:9]=1)=[O:5])[CH3:8]

Komponenten

5

Edukt 3

HCID 8929Sodium CyanideHCID 533707Ethyl isocyanoacetateHCID 11073343Methanethioic acid, O-ethyl ester

Produkt 1

HCID 5003096Ethyl thiazole-4-carboxylateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 4.52 g. (0.04 m) of ethyl isocyanoacetate and 3.60 g. (0.04 m) of ethyl thioformate in 15 ml. of absolute ethanol is added dropwise with vigorous stirring to a suspension of 0.25 g. of sodium cyanide in 10 ml. ethanol at 15° C. An exotherm developes during the addition and is moderated with ice-bath cooling. The reaction mixture is warmed at 50° C. for 30 minutes. The solvent is then removed in vacuo and the resulting residue extracted with several portions of hot hexane to give a 92% yield of 4-ethoxycarbonyl thiazole.

Aufarbeitung

  1. customat 15° C
  2. additionAn exotherm developes during the addition
  3. customis moderated with ice-bath
  4. temperaturecooling
  5. customThe solvent is then removed in vacuo
  6. extractionthe resulting residue extracted with several portions of hot hexane

Quellen und Nachweise

ORD-Eintrag
ord-33a99da0e1a449ccb8c0685184ff5362
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04021438

Notizen zur Reaktion

Wird geladen…