Reacción #2467988

Ecuación de reacción

2,5-dihydroxy-1,4-dithiane

cyanoacetamide

→

solid

Rendimiento 53.0%

2-Aminothiophene-3-carboxamide

Rendimiento 53.0%

Disolventes

ethanol

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was refluxed for 3 h
2. 2
   Otroattained to rt
3. 3
   OtroEthanol (appr. 150 mL) was removed under reduced pressure
4. 4
   workup.ADDITIONpoured the contents into ice cold water
5. 5
   ExtracciónThe solution was extracted with ethyl acetate (3×100 mL)
6. 6
   Lavadothe combined EtOAc layer was washed with water, brine
7. 7
   Secadodried over sodium sulfate
8. 8
   FiltraciónThe solution was filtered
9. 9
   Otroevaporated the solvent
10. 10
    OtroThe residue was chromatographed over silica gel column

Procedimiento

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.

Fuente