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Sulfuric Acid → Bis[3-(dibutylamino)propyl]5,6-dihydro-6-oxophenanthridine-3,8-dicarboxylate dihydrochloride

HRID 1580800
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1580800
[ClH:1].Cl.[CH2:3]([N:7]([CH2:43][CH2:44][CH2:45][CH3:46])[CH2:8][CH2:9][CH2:10][O:11][C:12]([C:14]1[CH:26]=[CH:25][C:24]2[C:23]3[C:18](=[CH:19][C:20]([C:27]([O:29][CH2:30][CH2:31][CH2:32][N:33]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH2:36][CH3:37])=[O:28])=[CH:21][CH:22]=3)[C:17](=[O:42])[C:16]=2[CH:15]=1)=[O:13])[CH2:4][CH2:5][CH3:6].S(=O)(=O)(O)O.[N-:52]=[N+]=[N-].[Na+]>FC(F)(F)C(O)=O>[ClH:1].[ClH:1].[CH2:38]([N:33]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:32][CH2:31][CH2:30][O:29][C:27]([C:20]1[CH:21]=[CH:22][C:23]2[C:24]3[C:16]([C:17](=[O:42])[NH:52][C:18]=2[CH:19]=1)=[CH:15][C:14]([C:12]([O:11][CH2:10][CH2:9][CH2:8][N:7]([CH2:3][CH2:4][CH2:5][CH3:6])[CH2:43][CH2:44][CH2:45][CH3:46])=[O:13])=[CH:26][CH:25]=3)=[O:28])[CH2:39][CH2:40][CH3:41]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 68140824Bis[3-(dibutylamino)propyl]9-oxo-fluorene-2,7-dicarboxylate dihydrochloride

Produkt 1

HCID 21543599Bis[3-(dibutylamino)propyl]5,6-dihydro-6-oxophenanthridine-3,8-dicarboxylate dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422
Trifluoroacetic acid
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 20.4 g (0.03 mole) of bis[3-(dibutylamino)propyl]9-oxo-fluorene-2,7-dicarboxylate dihydrochloride and 13 ml of concentrated sulfuric acid contained in 150 ml of trifluoroacetic acid, which has been cooled to 0°C., is slowly added 2.6 g (0.04 mole) of sodium azide with stirring. Stirring is continued for 30 minutes whereupon most of the trifluoroacetic acid is removed in vacuo. Cracked ice is added and the residue is made alkaline with a 50% sodium hydroxide solution. The reaction mixture is extracted with methylene chloride, the extracts are combined, dried over magnesium sulfate, filtered and the filtrate treated with a slight excess of ethereal hydrogen chloride. The solution is concentrated to approximately 300 ml in vacuo, and approximately 500 ml of warm butanone is added. The mixture is permitted to cool slowly whereupon the desired bis[3-(dibutylamino)propyl]5,6-dihydro-6-oxophenanthridine-3,8-dicarboxylate crystallizes as the dihydrochloride salt. The product when recrystallized from a methylene chloride-ethyl acetate mixture has a m.p. 204.5°-6.5°C., and a N.E. of 349.4.

Aufarbeitung

  1. stirringStirring
  2. customwhereupon most of the trifluoroacetic acid is removed in vacuo
  3. additionCracked ice is added
  4. extractionThe reaction mixture is extracted with methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. additionthe filtrate treated with a slight excess of ethereal hydrogen chloride
  8. concentrationThe solution is concentrated to approximately 300 ml in vacuo, and approximately 500 ml of warm butanone
  9. additionis added
  10. temperatureto cool slowly whereupon the desired bis[3-(dibutylamino)propyl]5,6-dihydro-6-oxophenanthridine-3,8-dicarboxylate
  11. customcrystallizes as the dihydrochloride salt
  12. customThe product when recrystallized from a methylene chloride-ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-e91d0faa10174ac385cacfe54870b94c
Quelldatensatz
uspto-grants-1976_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03933893

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