Reaktion #2071844

Reaktionsgleichung

ethyl 2-methylthiazole-4-carboxylate

sulfuric acid

iodine

iodic acid

sodium thiosulfate

→

title compound

Ausbeute 46.3%

5-Iodo-2-methyl-thiazole-4-carboxylic acid ethyl ester

Ausbeute 46.3%

Lösungsmittel

acetic acid

carbontetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe resulting reaction mixture
2. 2
   Extraktionwas extracted with ethyl acetate (1000 mL)
3. 3
   WaschenThe combined organic layers were washed with aqueous sodium carbonate (saturated, 1000 mL)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 20:80)

Vorschrift

To a solution of ethyl 2-methylthiazole-4-carboxylate (11.2 g, 65.4 mmol) in acetic acid (200 mL) were added sulfuric acid (30%, 20 mL), carbontetrachloride (30 mL), iodine (33.2 g, 131 mmol) and iodic acid (11.5 g, 65.4 mmol) and the resulting reaction mixture was stirred for 19 h at 80° C. After addition of aqueous sodium thiosulfate (1 M, 500 mL) it was extracted with ethyl acetate (1000 mL). The combined organic layers were washed with aqueous sodium carbonate (saturated, 1000 mL), dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 20:80) afforded the title compound (9.00 g, 37%) as a white crystalline solid. MS: m/e=298.1 [M+H]+.

Quelle