Ammonia → HCID 53933795, compound

HRID 2396059Notes

Reaction equation

HRID 2396059 reaction equation
CO[C:3](=[O:34])[C:4]1[C:5](=[CH:10][C:11]([N:24]([CH2:31][CH:32]=[CH2:33])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:12]([N:14]([CH2:21][CH:22]=[CH2:23])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1)[C:6]([O:8]C)=[O:7].[NH3:35]>CO>[CH2:31]([N:24]([C:11]1[CH:10]=[C:5]([C:6]([OH:8])=[O:7])[C:4](=[CH:13][C:12]=1[N:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:21][CH:22]=[CH2:23])[C:3]([NH2:35])=[O:34])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH:32]=[CH2:33]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 21753022HCID 21753022, compound

Product 1

HCID 53933795HCID 53933795, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

In an autoclave, 457 mg (1 mmol) of 4,5-bis(N-allylanilino)phthalic acid dimethyl ester are dissolved in 5 ml of methanol, and 15 ml of ammonia areused for the purpose of amide formation. The autoclave is closed and then heated at 120° C. for 24 hours, then cooled and opened, and the ammonia is driven off with nitrogen. The residue is rinsed out with ethyl acetate and filtered, and the filtrate is chromatographed on silica gel with hexane/ethyl acetate 3:1. The product fractions are concentrated by evaporation and crystallized from hexane/ethyl acetate, yielding the titlecompound in the form of yellow crystals, FAB-MS: 410 [M+ +H], m.p. 122°-127° C. As by product of the reaction, 4,5-Bis-(N-allyl-N-phenylamino)phthalic acid monoamide was isolated and recrystallized from hexane/ethyl acetate to yield yellow crystalIs, FAB-MS: 428 [M+ +H], m.p. 114°-116° C.

Workup

  1. customThe autoclave is closed
  2. temperaturecooled
  3. washThe residue is rinsed out with ethyl acetate
  4. filtrationfiltered
  5. customthe filtrate is chromatographed on silica gel with hexane/ethyl acetate 3:1
  6. concentrationThe product fractions are concentrated by evaporation
  7. customcrystallized from hexane/ethyl acetate
  8. customyielding the titlecompound in the form of yellow crystals, FAB-MS
  9. customAs by product of the reaction

Sources & evidence

ORD record
ord-1f6b952fda9248909b803f9f9e02de9e
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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