N,N-Diethyl-p-phenylenediamine → HCID 10346545, compound

HRID 2396048Notes

Reaction equation

HRID 2396048 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:10][C:9](O[Si](C)(C)C)=[C:8](O[Si](C)(C)C)[CH2:7][C:6]=1[C:21]([O:23][CH3:24])=[O:22])=[O:4].[CH2:25]([N:27]([C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)[CH2:28][CH3:29])[CH3:26]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:4])[C:5]1[C:6](=[CH:7][C:8]([NH:34][C:33]2[CH:32]=[CH:31][C:30]([N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])=[CH:36][CH:35]=2)=[C:9]([NH:34][C:33]2[CH:32]=[CH:31][C:30]([N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])=[CH:36][CH:35]=2)[CH:10]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 7120N,N-Diethyl-p-phenylenediamineHCID 10022190HCID 10022190, compound

Product 1

HCID 10346545HCID 10346545, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a) and 3.94 g (24 mmol) of 4-(N,N-diethyl-amino)-aniline in 24 ml of glacial acetic acid is boiled under reflux for 2 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane and the solution is washed in succession with 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed onsilica gel with dichloromethane/methanol 400:15 and the product fractions are concentrated by evaporation and again chromatographed on silica gel with ethyl acetate/hexane 1:1. The product fractions are concentrated by evaporation, yielding the title compound in the form of green crystals, FAB-MS: 518 [M+ ], 519 [M+ +H].

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated off
  4. dissolutionthe dark-brown residue is dissolved in dichloromethane
  5. washthe solution is washed in succession with 50 ml of saturated NaHCO3 and twice with 20 ml of water
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customThe evaporation residue is chromatographed onsilica gel with dichloromethane/methanol 400:15
  9. concentrationthe product fractions are concentrated by evaporation
  10. customagain chromatographed on silica gel with ethyl acetate/hexane 1:1
  11. concentrationThe product fractions are concentrated by evaporation

Sources & evidence

ORD record
ord-762a6479de0642b6b1fd1ab1811c0429
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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