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

HRID 441935Notes

Reaction equation

HRID 441935 reaction equation
[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]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 12698223N,N'-(1-Phenylethane-1,2-diyl)diacetamide

Product 1

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

Procedure

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.

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. dry with materialthat was dried with MgSO4
  3. customevaporated to dryness under reduced pressure
  4. customThe product was recrystallized from acetone/hexane

Sources & evidence

ORD record
ord-84079c942a4e4614a42603079a367309
Source dataset
uspto-grants-1977_08
Patent number
US04043998

Reaction notes

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