Ethyl 2-amino-5-methylthiazole-4-carboxylate → Ethyl 5-methylthiazole-4-carboxylate

HRID 2427266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2427266
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](N)[S:9][C:10]=1[CH3:11])=[O:5])[CH3:2]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

Komponenten

3

Edukt 1

HCID 766578Ethyl 2-amino-5-methylthiazole-4-carboxylate

Produkt 1

HCID 12300671Ethyl 5-methylthiazole-4-carboxylateAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a 3-neck round bottom flask mix 2-amino-5-methyl-thiazole-4-carboxylic acid ethyl ester (62.9 g, 338 mmol) and THF (630 mL). Heat to reflux and treat the reaction mixture with isoamyl nitrile (52.6 g, 60.1 mL, 449 mmol) dropwise. Upon completion of the addition, stir the reaction at reflux for 1 h, then concentrate the reaction mixture by rotavap (hi-vac) to give 70 g crude product as a thick orange oil. Purify on silica gel (400 g, 20-45% EtOAc/hexanes) to afford 39.47 g (68%) of the title compound as a yellow solid. LC-ES/MS m/z 172 (M+1), TR=1.5 min.

Aufarbeitung

  1. temperatureHeat
  2. temperatureto reflux
  3. additionUpon completion of the addition
  4. customthe reaction
  5. temperatureat reflux for 1 h
  6. concentrationconcentrate the reaction mixture by rotavap (hi-vac)
  7. customto give 70 g crude product as a thick orange oil
  8. customPurify on silica gel (400 g, 20-45% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b5c31610baad4facb5551c2f4149a3cc
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968587B2

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