Water → 9H-Indeno[1,2-b]pyrazine-2,3,9(1H, 4H)-trione 9-ethylene dithioacetal

HRID 129454

Reaktionsgleichung

Reaktionsgleichung von HRID 129454
[NH:1]1[C:6](=O)[C:5](=[O:8])[NH:4][C:3]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:15](=[O:16])[C:2]1=2.O.[CH2:18]([SH:21])[CH2:19][SH:20].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH2:18]1[S:21][C:6]2([C:5](=[O:8])[NH:4][C:3]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:15](=[O:16])[C:2]=3[NH:1]2)[S:20][CH2:19]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 190359779H-Indeno[1,2-b]pyrazine-2,3,9(1H,4H)-trione

Produkt 1

HCID 867491119H-Indeno[1,2-b]pyrazine-2,3,9(1H, 4H)-trione 9-ethylene dithioacetalAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A suspension of 9H-indeno[1,2-b]pyrazine-2,3,9(1H, 4H)-trione. 0.9 H2O (2.0 g, 8.68 mmol) in toluene (50 ml), 1,2-ethanedithiol (2.19 ml, 26.04 mmol) and boron trifluoride etherate (1.07 ml, 8.68 mmol) was refluxed for 20 hours. The reaction mixture was cooled to room temperature, and the precipitate was filtered off and washed with toluene, ethanol-water (2:1) and ethanol. The crude material (2.40 g) was recrystallized from DMF-water to give 2.09 g (83%) of the title compound. M.p. >300° C. 1H-NMR (DMSO-d6, δ): 3.68 (m, 2H), 3.91 (m, 2H), 7.2 (t, 1H), 7.3 (t, 1H), 7.51 (d, 1H), 7.59 (d, 1H), 12.05 (s, 1H), 12.38 (s, 1H).

Aufarbeitung

  1. filtrationthe precipitate was filtered off
  2. washwashed with toluene, ethanol-water (2:1) and ethanol
  3. customThe crude material (2.40 g) was recrystallized from DMF-water

Quellen und Nachweise

ORD-Eintrag
ord-e3791f7b9e7e4eae98cbd9f962e98b24
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468748

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