반응 #45822

반응 방정식

ammonia

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

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

hydroxybenzotriazole

→

compound

수율 99.1%

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

수율 99.1%

용매

N,N-dimethylformamide

반응 조건

후처리

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

실험 절차

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.

출처