Ethyl (chloroformyl)acetate → Ethyl thiazole-5-carboxylate

HRID 235340

Reaktionsgleichung

Reaktionsgleichung von HRID 235340
[CH:1]([NH2:3])=[S:2].Cl[CH:5]([CH:11]=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7]>CC(C)=O>[S:2]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][N:3]=[CH:1]1

Komponenten

4

Edukt 2

HCID 118030Ethyl (chloroformyl)acetateHCID 3005587Methanethioamide

Produkt 1

HCID 459108Ethyl thiazole-5-carboxylateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a round bottom flask was added 250 mL of dry acetone, 7.5 g (0.123 mol) of thioformamide, and 18.54 g (0.123 mol) of ethyl 2-chloro-2-formylacetate. The reaction was heated at reflux for 2 hours. The solvent was removed in vacuo, and the residue was purified by chromatography (SiO2, 6 cm o.d. column, 100% CHCl3, Rf =0.25) to provide 11.6 g (60%) of the desired compound as a light yellow oil. NMR (CDCl3) δ1.39 (t, J=7 Hz, 3H), 4.38 (q, J=7 Hz, 2H), 8.50 (s, 1H), 8.95 (s, 1H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by chromatography (SiO2, 6 cm o.d

Quellen und Nachweise

ORD-Eintrag
ord-44f70e42d0264fd79a876b52447a3202
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597928

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