Реакция #45822

Уравнение реакции

ammonia

1-Ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride

4-bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylic acid

hydroxybenzotriazole

→

compound

Выход 99.1%

4-Bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxamide

Выход 99.1%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe reaction liquid
2. 2
   Температураwas cooled at 0° C.
3. 3
   workup.STIRRINGby further stirring at room temperature for 1 hour
4. 4
   ДругоеThe reaction liquid
5. 5
   Концентрированиеwas concentrated under reduced pressure
6. 6
   workup.ADDITIONsaturated sodium bicarbonate water (200 ml) was added
7. 7
   Экстракцияthe product was extracted with ethyl acetate (200 ml×2)
8. 8
   ПромывкаThe organic layer was washed with saturated brine (50 ml)
9. 9
   Сушкаdried over anhydrous magnesium sulfate
10. 10
    Концентрированиеconcentrated under reduced pressure
11. 11
    Другоеthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3:2)

Методика

1-Ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (1.61 g, 8.42 mmol) was added to an N,N-dimethylformamide (80 ml) solution of 4-bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylic acid (I-256) (2.62 g, 7.02 mmol) and hydroxybenzotriazole (1.14 g, 8.42 mmol), followed by stirring at room temperature for 1 hour. The reaction liquid was cooled at 0° C., then aqueous 28% ammonia (1.42 ml, 21.1 mmol) was put into it, followed by further stirring at room temperature for 1 hour. The reaction liquid was concentrated under reduced pressure, then saturated sodium bicarbonate water (200 ml) was added, the product was extracted with ethyl acetate (200 ml×2). The organic layer was washed with saturated brine (50 ml), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3:2) to obtain the entitled compound (2.59 g, 99%) as a yellow white solid.

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