Реакция #2467988

Уравнение реакции

2,5-dihydroxy-1,4-dithiane

cyanoacetamide

→

solid

Выход 53.0%

2-Aminothiophene-3-carboxamide

Выход 53.0%

Растворители

ethanol

triethylamine

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was refluxed for 3 h
2. 2
   Другоеattained to rt
3. 3
   ДругоеEthanol (appr. 150 mL) was removed under reduced pressure
4. 4
   workup.ADDITIONpoured the contents into ice cold water
5. 5
   ЭкстракцияThe solution was extracted with ethyl acetate (3×100 mL)
6. 6
   Промывкаthe combined EtOAc layer was washed with water, brine
7. 7
   Сушкаdried over sodium sulfate
8. 8
   ФильтрацияThe solution was filtered
9. 9
   Другоеevaporated the solvent
10. 10
    ДругоеThe residue was chromatographed over silica gel column

Методика

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.

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