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

反応式

[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]

参加物

反応物 3

HCID 944Nitric Acid

HCID 516892Sodium Bicarbonate

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

生成物 1

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

実験手順

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.