Boron trifluoride etherate → 9H-Indeno[1,2-b]pyrazine-3,9(4H)-dione 9-ethylene dithioacetal

HRID 263910

Reaktionsgleichung

Reaktionsgleichung von HRID 263910
[N:1]1[C:2]2[C:14](=[O:15])[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:3]=2[NH:4][C:5](=O)[CH:6]=1.[CH2:16]([SH:19])[CH2:17][SH:18].B(F)(F)F.CCOCC>C1C=CC=CC=1>[CH2:16]1[S:19][C:5]2([NH:4][C:3]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[C:14](=[O:15])[C:2]=3[N:1]=[CH:6]2)[S:18][CH2:17]1

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 190359769H-Indeno[1,2-b]pyrazine-3,9(4H)-dione

Produkt 1

HCID 867491109H-Indeno[1,2-b]pyrazine-3,9(4H)-dione 9-ethylene dithioacetalAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A suspension of 9H-indeno[1,2-b]pyrazine-3,9(4H)-dione (0.50 g, 2.52 mmol) in benzene (10 ml), 1,2-ethanedithiol (0.63 ml, 7.56 mmol) and boron trifluoride etherate (0.31 ml, 2.52 mmol) was refluxed for 23 hours. The reaction mixture was cooled to room temperature, and the precipitate was filtered off and washed with benzene and water and dried. The crude material (0.64 g) was recrystallized twice from ethanol to give 0.44 g (64%) of the title compound. M.p. 284°-290° C. 1 -NMR (DMSO-d6, δ): 3.75-3.94 (m, 4H), 7.46-7.57 (m, 2H), 7.8 (m, 2H), 7.95 (s, 1H), 12.6 (s, 1H).

Aufarbeitung

  1. temperaturewas refluxed for 23 hours
  2. filtrationthe precipitate was filtered off
  3. washwashed with benzene and water
  4. customdried
  5. customThe crude material (0.64 g) was recrystallized twice from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-48c01f9bfca7409cb30856e8cf26f9a9
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646146

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