Реакция #2467979

Уравнение реакции

water

ethylenediamine

methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate

sodium chloride

→

product

Выход 22.0%

N-(2-aminoethyl){3-[(dimethylamino)diazenyl](2-thienyl)}-carboxamide

Выход 22.0%

Растворители

ethanol

ethanol

Условия реакции

Обработка

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   ЭкстракцияThe solution was extracted with THF (3×100 mL)
3. 3
   ПромывкаThe combined THF layer was washed with 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 ethylenediamine (5 mL) in ethanol (5 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (250 mg) in ethanol (5 mL) for 5 min and stirred at rt for 24 h. The solution was poured into ice cooled water and saturated with sodium chloride. The solution was extracted with THF (3×100 mL). The combined THF layer was washed with 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 (90:10) as eluents to give the product as an off-white solid (60 mg, 22%), mp 98-100° C. 1H NMR (400 MHz, CDCl3): δ 8.65 (1H, br s), 7.30 (1H, d, J=5.2 Hz), 7.28 (1H, d, J=5.2 Hz), 3.50-3.57 (5H, m). 3.24 (3H, br s), 2.91 (2H, t, J=6.0 Hz).

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