Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 515654, compound

HRID 268137Notes

Reaction equation

HRID 268137 reaction equation
[CH:1]1[C:15]2=[C:16]3[C:8]([C:9]4[C:14]2=[CH:13][C:12]([C:17](Cl)=[O:18])=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=[C:3]([C:20](Cl)=[O:21])[CH:2]=1.[CH2:23]([N:26]([CH2:31][CH:32]=[CH2:33])[CH2:27][CH2:28][CH2:29][OH:30])[CH:24]=[CH2:25].[C:34]1([NH2:45])[C:39](F)=[C:38](F)C(F)=C(N)C=1F.Cl.Cl>C(Cl)(Cl)Cl>[CH2:31]([N:26]([CH2:23][CH:24]=[CH2:25])[CH2:27][CH2:28][CH2:29][O:30][C:20]([C:3]1[CH:2]=[CH:1][C:15]2[C:14]3[C:9]([C:8]4[C:16]=2[C:4]=1[CH:5]=[CH:6][CH:7]=4)=[CH:10][CH:11]=[C:12]([C:17]([O:18][CH2:17][CH2:12][CH2:11][N:45]([CH2:34][CH:39]=[CH2:38])[CH2:15][CH:1]=[CH2:2])=[O:18])[CH:13]=3)=[O:21])[CH:32]=[CH2:33]

Participants

5

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 147826653-[Di(prop-2-en-1-yl)amino]propan-1-olHCID 21419635HCID 21419635, compound

Product 1

HCID 515654HCID 515654, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 500 ml of chloroform is added 9.8 g (0.03 mole) of fluoranthene-3,9-dicarbonyl chloride and 9.3 g (0.06 mole) of 3-diallylaminopropanol and the solution is refluxed for 16 hours. The dihydrochloride salt is converted to the free base by treating the chloroform solution with saturated aqueous sodium bicarbonate, separation of the organic and water layer, drying the organic layer over anhydrous magnesium sulfate and finally removing the solvent in vacuo. The residue is dissolved in butanone and acidified with ethereal hydrogen chloride. The salt is crystallized twice from methanol-butanone or water-methanol-butanone, M.P. 229°-231°C, and converted back to the free base to give a yellow viscous oil of bis(3-diallylaminopropyl)fluoranthene-3,9-dicarboxylate, λmax 0.1 NHCl 229 m μ, E1 cm 1% 605.

Workup

  1. temperaturethe solution is refluxed for 16 hours
  2. customwith saturated aqueous sodium bicarbonate, separation of the organic and water layer
  3. dry with materialdrying the organic layer over anhydrous magnesium sulfate
  4. customfinally removing the solvent in vacuo
  5. dissolutionThe residue is dissolved in butanone
  6. customThe salt is crystallized twice from methanol-butanone or water-methanol-butanone, M.P. 229°-231°C

Sources & evidence

ORD record
ord-d2ec39634eaf451999f26ecda7112164
Source dataset
uspto-grants-1976_03
Patent number
US03946112

Reaction notes

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