Реакция #2467977

Уравнение реакции

water

ethanol amine

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

→

solid

Выход 77.0%

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

Выход 77.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Экстракцияthe solution was extracted with ethyl acetate (3×50 mL)
3. 3
   ПромывкаThe combined EtOAc 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
8. 8
   Другоеto give the product, which
9. 9
   Другоеwas recrystallized from chloroform-hexane

Методика

To an ice cold (0-5° C.) solution of ethanol amine (5 mL) in THF (5 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (500 mg) in THF (5 mL) for 5 min and stirred at rt for 20 h. The solution was poured into ice cooled water and the solution was extracted with ethyl acetate (3×50 mL). 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, which was recrystallized from chloroform-hexane gave the product as a pale orange color solid (430 mg, 77%), mp 118-122° C. IR (neat) νmax, 3397, 3278, 2926, 1621, 1353, 1298, 1220, 1083, 1007, 882, 775 cm−1;

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