Aniline → Propanediamide, N,N'-diphenyl-

HRID 2199000Notes

Reaction equation

HRID 2199000 reaction equation
[C:1]1(=[O:6])O[C:3](=[O:4])[CH2:2]1.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:1]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])[CH2:2][C:3]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

3

Reactant 2

HCID 6115AnilineHCID 10176090Malonic anhydride

Product 1

HCID 69298Propanediamide, N,N'-diphenyl-Yield 72%

Procedure

To the cold solution of malonic anhydride, prepared as above, was added aniline (700 μl, 6 equivalents). The reaction mixture was allowed to warm to room temperature. It was then extracted with 5 ml saturated aqueous NaHCO3, and the aqueous extract was washed with 5 ml ether, acidified with H2SO4, and extracted with 3-4-ml portions of ether. The ether extracts were combined and dried over Na2SO4, and the ether was removed under reduced pressure, to leave a residue of malonanilide (mp 127°-130° C., 180 mg, 72% isolated yield, based on diketone).

Workup

  1. extractionIt was then extracted with 5 ml saturated aqueous NaHCO3
  2. extractionthe aqueous extract
  3. washwas washed with 5 ml ether
  4. extractionextracted with 3-4-ml portions of ether
  5. dry with materialdried over Na2SO4
  6. customthe ether was removed under reduced pressure

Sources & evidence

ORD record
ord-0891e1a5b60f4f00b2aae061a6b0651a
Source dataset
uspto-grants-1982_11
Patent number
US04360691

Reaction notes

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