Reaktion #1980535

Reaktionsgleichung

trans-4-thiocarbamoyl-cyclohexanecarboxylic acid methyl ester

thioacetamide

iodine

→

title compound

Ausbeute 5.8%

trans-4-(5-Methyl-[1,2,4]thiadiazol-3-yl)-cyclohexanecarboxylic acid methyl ester

Ausbeute 5.8%

Lösungsmittel

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas partitioned between 0.1 M sodium thiosulfate solution (100 ml) and ethyl acetate (100 ml)
2. 2
   SonstigeThe layers were separated
3. 3
   ExtraktionThe aqueous layer was extracted with two 50-ml portions of ethyl acetate
4. 4
   TrocknenThe combined organic layers were dried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   workup.DISTILLATIONThe residue was purified by Kugelrohr distillation
7. 7
   workup.DISTILLATIONThe distillate was purified by flash-chromatography with n-heptane/tert-butyl methyl ether as eluent

Vorschrift

To a solution of trans-4-thiocarbamoyl-cyclohexanecarboxylic acid methyl ester (0.30 g, 1.5 mmol) and thioacetamide (0.67 g, 8.9 mmol) in methanol (7 ml) was added a solution of iodine (2.65 g, 10.4 mmol) in methanol (15 ml) at room temperature. After stirring for 48 h the reaction mixture was partitioned between 0.1 M sodium thiosulfate solution (100 ml) and ethyl acetate (100 ml). The layers were separated. The aqueous layer was extracted with two 50-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by Kugelrohr distillation. The distillate was purified by flash-chromatography with n-heptane/tert-butyl methyl ether as eluent to give the title compound (0.021 g, 5%) as light yellow oil, which was contaminated with 20% trans-4-(3-methyl-[1,2,4]thiadiazol-5-yl)-cyclohexanecarboxylic acid methyl ester. MS m/e: 241 ([M+H]+)

Quelle