Реакция #2467966

Уравнение реакции

water

ammonium hydroxide

methyl 3-[(dimethylamino)diazenyl]-5-nitrothiophene-2-carboxylate

→

solid

Выход 26.0%

3-[(Dimethylamino)diazenyl]-5-nitrothiophene-2-carboxamide

Выход 26.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Экстракцияextracted with ethyl acetate (3×100 mL)
3. 3
   ПромывкаThe combined organic layer was washed with water, brine
4. 4
   Сушкаdried over sodium sulfate
5. 5
   ФильтрацияThe solution was filtered
6. 6
   Другоеevaporated the solvent
7. 7
   ДругоеThe residue was chromatographed over silica gel column

Методика

To an ice cold (0-5° C.) solution of ammonium hydroxide (35 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]-5-nitrothiophene-2-carboxylate (400 mg) in THF (10 mL) for 5 min and stirred at rt for 20 h. The solution was poured into ice cooled water and extracted with ethyl acetate (3×100 mL). The combined organic 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 hexane-ethyl acetate (50:50) as eluents to give the product as a yellow color solid (90 mg, 26%), mp 240-246° C. 1H NMR (400 MHz, DMSO-d6): δ 8.22 (1H, s), 8.05 (1H, s), 7.91 (1H, s), 3.63 (3H, s), 3.26 (3H, s); LC-MS (positive ion mode): m/z 266 (M+Na)+.

Источник