4,5-Dianilinophthalimide → HCID 22918413, compound

HRID 2396058Notes

Reaction equation

HRID 2396058 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[NH:23]([C:30]1[CH:31]=[C:32]2[C:37](=[O:38])[NH:36][C:34](=O)[C:33]2=[CH:39][C:40]=1[NH:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[NH:23]([C:30]1[CH:31]=[C:32]2[C:37](=[O:38])[NH:36][C:34](=[S:10])[C:33]2=[CH:39][C:40]=1[NH:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 16974,5-DianilinophthalimideHCID 87949Lawesson's reagent

Product 1

HCID 22918413HCID 22918413, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

138 mg (0.36 mmol) of Lawesson reagent [=2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiaphosphetane] are added to a solution of 100 mg (0.3 mmol) of 4,5-bis-(anilino)phthalimide (Example 1) in 15 ml of dichloromethane and the mixture is boiled under reflux for 4 hours. The reaction mixture is concentrated by evaporation and chromatographed directly on silica gel with hexane/ethyl acetate 2:1. The product fractions are concentrated by evaporation, yielding the title compound in the form of yellow crystals, FAB-MS: 346 [M+ +H].

Workup

  1. temperatureunder reflux for 4 hours
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. customchromatographed directly on silica gel with hexane/ethyl acetate 2:1
  4. concentrationThe product fractions are concentrated by evaporation

Sources & evidence

ORD record
ord-e87bb541f1894a22985986fefa2d8434
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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