Reaktion #2467988

Reaktionsgleichung

2,5-dihydroxy-1,4-dithiane

cyanoacetamide

→

solid

Ausbeute 53.0%

2-Aminothiophene-3-carboxamide

Ausbeute 53.0%

Lösungsmittel

ethanol

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 3 h
2. 2
   Sonstigeattained to rt
3. 3
   SonstigeEthanol (appr. 150 mL) was removed under reduced pressure
4. 4
   workup.ADDITIONpoured the contents into ice cold water
5. 5
   ExtraktionThe solution was extracted with ethyl acetate (3×100 mL)
6. 6
   Waschenthe combined EtOAc layer was washed with water, brine
7. 7
   Trocknendried over sodium sulfate
8. 8
   FiltrationThe solution was filtered
9. 9
   Sonstigeevaporated the solvent
10. 10
    SonstigeThe residue was chromatographed over silica gel column

Vorschrift

To a solution of 2,5-dihydroxy-1,4-dithiane (10 g, 65.78 mmol) in ethanol (200 mL) and triethylamine (2 mL) was added cyanoacetamide (5.52 g, 65.78 mmol) at rt for 5 min. The reaction mixture was refluxed for 3 h and attained to rt. Ethanol (appr. 150 mL) was removed under reduced pressure and poured the contents into ice cold water and stirred for 15 min. The solution was extracted with ethyl acetate (3×100 mL) and the combined EtOAc layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform-methanol (95:5) as eluents to give the product as a pale yellow color solid (4.9 g, 53%), mp 150-152° C.

Quelle