反应详情

温度

0 °C

Under a N2 atmosphere was added 1.97 g (15.6 mmol) of oxalyl chloride to 3 ml of dry toluene which was cooled to 0° C. To this solution was added 3.55 g (15.6 mmol) of N-1-adamantylaniline in toluene (8 ml). The reaction was allowed to stir for 30 min. at 0° C. and then heated at 65° C. for 3 hours. Additional solvent (10 ml) was added and the reaction was kept at 65° C. for 72 hours. The solvent was removed and the residue was allowed to stir at 160° C. for 5 hours. The crude reaction mixture was allowed to cool and was chromatographed on silica gel using 6:1 hexane:EtOAc to afford crude product, which was triturated with isopropyl ether (IPE) to generate 164 mg (4.4%) of 1-adamantylisatin combined with product contaminated with significant amounts of impurities.

1. temperatureheated at 65° C. for 3 hours
2. waitthe reaction was kept at 65° C. for 72 hours
3. customThe solvent was removed
4. stirringto stir at 160° C. for 5 hours
5. customThe crude reaction mixture
6. temperatureto cool
7. customwas chromatographed on silica gel using 6:1 hexane
8. customEtOAc to afford crude product, which
9. customwas triturated with isopropyl ether (IPE)