Ethyl bromopyruvate → Ethyl 2-cyclobutylthiazole-4-carboxylate

HRID 1609330

Reaktionsgleichung

Reaktionsgleichung von HRID 1609330
[CH:1]1([C:5](=[S:7])[NH2:6])[CH2:4][CH2:3][CH2:2]1.Br[CH2:9][C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:14]([O:13][C:11]([C:10]1[N:6]=[C:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)[S:7][CH:9]=1)=[O:12])[CH3:15]

Komponenten

5

Edukt 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 22141088Cyclobutanecarbothioamide

Produkt 1

HCID 54513950Ethyl 2-cyclobutylthiazole-4-carboxylateAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture composed of 9.7 g of cyclobutancarbothioamide, 16.5 g of ethyl bromopyruvate and 200 ml of ethyl alcohol was heated to reflux for 1 hr. The reaction mixture was partially condensed in vacuo and the residual materials were diluted with ice water and and excess of saturated sodium bicarbonate solution. The solids were collected to yield 7.0 g of 2-cyclobutyl-4-thiazolecarboxylic acid ethyl ester; m.p. 48°-50° C. after recrystallization from pentane.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 1 hr
  3. customcondensed in vacuo
  4. customThe solids were collected

Quellen und Nachweise

ORD-Eintrag
ord-df771a0a379b406ea2b9b346b05952b7
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05399702

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