반응 #654017

반응 방정식

Hydrazine hydrate

1,2-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-4,5-dinitrobenzene

CH2Cl2 MeOH

→

1,2-diamino-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzene

수율 89.0%

용매

EtOH

ethanol

반응 조건

후처리

1. 1
   기타In an oven dried 500 mL round bottom flask
2. 2
   기타equipped with a Claisen adapter, pressure
3. 3
   온도reflux condenser
4. 4
   온도the dark black suspension is heated
5. 5
   온도to reflux under an argon atmosphere
6. 6
   온도The resulting brown suspension is heated
7. 7
   온도at reflux for 1.5 h at which time the reaction mixture
8. 8
   여과Therefore, the mixture is hot filtered through Celite
9. 9
   세척the pad rinsed with absolute ethanol (50 mL)
10. 10
    기타The solvent is removed under reduced pressure
11. 11
    기타the resulting light brown oil is 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 (Formula E) (20 g, 0.04 mol) is dissolved in absolute ethanol (200 mL). To this clear solution, 10% palladium on carbon (4 g) is added and the dark black suspension is heated to reflux under an argon atmosphere. Hydrazine hydrate (20 mL) in EtOH (20 mL) is added dropwise over 10 min to avoid bumping. The resulting brown suspension is heated at reflux for 1.5 h at which time the reaction mixture is colorless and TLC analysis (95/5; CH2Cl2/MeOH) displays a low R∫UV active spot corresponding to the diamine. Therefore, the mixture is hot filtered through Celite and the pad rinsed with absolute ethanol (50 mL). The solvent is removed under reduced pressure and the resulting light brown oil is 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 (Formula F). For Formula F: FAB MS,M+: m/e 432; HRMS, M+: 432.2471 (calcd. for C20H36N2O8, 432.2482). This material is taken to the next step without further purification.

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