Nitric Acid → N,N'-[1-(4-Nitrophenyl)ethane-1,2-diyl]diacetamide

Reaktionsgleichung

[C:1]([NH:4][CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][NH:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].C([O-])(O)=O.[Na+].[N+:22]([O-])([OH:24])=[O:23]>>[C:1]([NH:4][CH:5]([C:11]1[CH:12]=[CH:13][C:14]([N+:22]([O-:24])=[O:23])=[CH:15][CH:16]=1)[CH2:6][NH:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2]

Komponenten

Edukt 3

HCID 944Nitric Acid

HCID 516892Sodium Bicarbonate

HCID 12698223N,N'-(1-Phenylethane-1,2-diyl)diacetamide

Produkt 1

HCID 13050187N,N'-[1-(4-Nitrophenyl)ethane-1,2-diyl]diacetamideAusbeute 61 %

Versuchsvorschrift

3 g, 0.014 mol of N,N'-Diacetyl-1-phenylethylenediamine was added slowly to 10 ml of 90% HNO3 at -40°. After stirring 5 hr at -40°, the solution was poured over ice and neutralized with NaHCO3. The product was extracted into ethyl acetate, and that was dried with MgSO4 and then evaporated to dryness under reduced pressure. The product was recrystallized from acetone/hexane, yielding 2.2 g (61%) of N,N'-Diacetyl-1-(p-nitrophenyl)-ethylenediamine mp 178°-180°. Anal. (C12H15N3O4) C, H, N were within 0.4% of theoretical.