반응 #161387

반응 방정식

hydrogen

sodium hydrogen carbonate

1-adamantylamine

2-(4-fluoro-3-nitrophenyl)benzoxazole

→

title compound

수율 16.1%

2-(2-(1-adamantylamino)anilin-5-yl)benzoxazole

수율 16.1%

용매

tetrahydrofuran

water

ethanol

반응 조건

후처리

1. 1
   온도this was heated
2. 2
   온도to reflux
3. 3
   여과the precipitated crystals were filtered off
4. 4
   세척washed with water
5. 5
   기타dried
6. 6
   기타The crystals obtained
7. 7
   workup.STIRRINGthis was stirred at room temperature for 6 hours
8. 8
   여과this was filtered through Celite
9. 9
   농축the filtrate was concentrated
10. 10
    기타The residue obtained
11. 11
    기타was purified by silica gel column chromatography

실험 절차

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added sodium hydrogen carbonate (195 mg, 2.32 mmol) and 1-adamantylamine (185 mg, 1.22 mmol), and this was heated to reflux with stirring for 4 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered off, washed with water and then dried. The crystals obtained were added to a tetrahydrofuran (5 mL) solution containing 10% palladium-carbon (100 mg), a hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 6 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (67.0 mg, 16% yield) as brown crystals.

출처