Ammonia → HCID 22918378, compound

HRID 1376774Notes

Reaction equation

HRID 1376774 reaction equation
C[O:2][C:3](=O)[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](OC)=[O:7].[NH3:35]>CO>[CH2:21]([N:14]([C:12]1[CH:13]=[C:4]2[C:3](=[O:2])[NH:35][C:6](=[O:7])[C:5]2=[CH:10][C:11]=1[N:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:31][CH:32]=[CH2:33])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:22]=[CH2:23]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 21753022HCID 21753022, compound

Product 1

HCID 22918378HCID 22918378, 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 are Used 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 title compound in the form of yellow crystals, FAB-MS: 410 [M+ +H], m.p. 122°-127° C. As byproduct of the reaction, 4,5-Bis-(N-allyl-N-phenylamino)phthalic acid monoamide was isolated and recrystallized from hexane/ethyl acetate to yield yellow crystals, 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

Sources & evidence

ORD record
ord-5003c442db844a93be5b5ec32e7d5b64
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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