Phosphorus oxychloride → 3,8-Di-(pyrrolidinomethyleneamino)-6(5H)-phenanthridone

HRID 745662

Reaktionsgleichung

Reaktionsgleichung von HRID 745662
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([C:12](=[O:16])[NH:13][C:14]=2[CH:15]=1)=[CH:10][C:9]([NH2:17])=[CH:8][CH:7]=3.P(Cl)(Cl)(Cl)=O.[CH:23]([N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)=O.C(Cl)(Cl)Cl.CO>O1CCCC1>[N:25]1([CH:23]=[N:1][C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[C:11]([C:12](=[O:16])[NH:13][C:14]=3[CH:15]=2)=[CH:10][C:9]([N:17]=[CH:23][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:8][CH:7]=4)[CH2:29][CH2:28][CH2:27][CH2:26]1

Komponenten

6

Edukt 4

HCID 24813Phosphorus oxychlorideHCID 773721-PyrrolidinecarboxaldehydeHCID 2837163,8-Diamino-5H-phenanthridin-6-oneHCID 21584188Chloroform methanol

Produkt 1

HCID 133458733,8-Di-(pyrrolidinomethyleneamino)-6(5H)-phenanthridoneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A suspension of 3,8-diamino-6-(5H)-phenanthridone (500 mg) in tetrahydrofuran (5 ml) was added to a mixture of phosphorus oxychloride (0.75 ml) and N-formylpyrrolidine (2.5 ml) and tetrahydrofuran (5 ml), the temperature of the mixture being kept at 5° C. The resulting mixture was stirred for 30 minutes at room temperature, heated at 50° C. for 1 hour and worked as described in Example 8, paragraph 1. Yield 52%, melting point 280° C. (decomposition) (CHCl3 /methanol).

Aufarbeitung

  1. custombeing kept at 5° C
  2. temperatureheated at 50° C. for 1 hour

Quellen und Nachweise

ORD-Eintrag
ord-72abbf7032ed4faa95680a74f33b4c58
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04599409

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