반응 #1166465
ord-101f51415fc144e99893f1202580d44b
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후처리
- 1기타In an oven dried 500 mL round bottom flask
- 2기타equipped with a Claisen adapter, pressure
- 3온도reflux condenser
- 4온도the dark black suspensions was heated
- 5온도to reflux under an argon atmosphere
- 6온도The resulting brown suspension was heated
- 7온도at reflux for 1.5 h at which time the reaction mixture
- 8여과Therefore, the mixture was hot filtered through Celite
- 9세척the pad rinsed with absolute ethanol (50 mL)
- 10기타The solvent was removed under reduced pressure
- 11기타the resulting light brown oil was dried in vacuo (in the dark) for 24 h
실험 절차
In an oven dried 500 mL round bottom flask, equipped with a Claisen adapter, pressure equalizing dropping funnel, and reflux condenser, 1,2-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-4,5-dinitrobenzene 1E (20 g, 0.04 mol) was dissolved in absolute ethanol (200 mL). To this clear solution, 10% palladium on carbon (4 g) was added and the dark black suspensions was heated to reflux under an argon atmosphere. Hydrazine hydrate (20 mL) in EtOH (20 mL) was added dropwise over 10 min to avoid bumping. The resulting brown suspension was heated at reflux for 1.5 h at which time the reaction mixture was colorless and TLC analysis (95/5; CH2Cl2 /MeOH) displayed a low RfUV active spot corresponding to the diamine. Therefore, the mixture was hot filtered through Celite and the pad rinsed with absolute ethanol (50 mL). The solvent was removed under reduced pressure and the resulting light brown oil was dried in vacuo (in the dark) for 24 h to yield 15.55 g (89%) of 1,2-diamino-bis [2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzene 1F. For 1F : FAB MS, M+ : m/e 432; HRMS, M+ : 432.2471 (calcd. for C20H36N2O8, 432.2482). This material was taken to the next step without further purification.