p-Toluenesulfonic acid → 9-(2,2-Bis(4-chlorophenyl))ethoxy-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dione

HRID 129456

Reaktionsgleichung

Reaktionsgleichung von HRID 129456
[OH:1][CH:2]1[C:14]2[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:25]O)=[CH:20][CH:19]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH:24]([C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)[CH2:25][O:1][CH:2]2[C:14]3[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]2=3)=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 175334-Chloro-beta-(4-chlorophenyl)benzeneethanolHCID 190359859-Hydroxy-9H-indeno[1,2-b]pyrazine-2,3(1H,4H)-dione

Produkt 1

HCID 537438169-(2,2-Bis(4-chlorophenyl))ethoxy-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dioneAusbeute 17,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A suspension of 9-hydroxy-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dione. 1H2O (0.50 g, 2.13 mmol) in acetic acid (30 ml), 2,2-bis(4-chlorophenyl)ethanol (2.84 g, 10.65 mmol) and p-toluensulfonic acid (20 mg) was refluxed for 21 hours. The reaction mixture was evaporated in vacuo to dryness, the residue was suspended in ethanol (40 ml) and the precipitate was filtered off and washed with ethanol and dried to give 0.39 g of the crude product, which was recrystallized from ethanol to yield 0.174 g (17.5%) of the title compound. M.p. 234°-237° C. 1H-NMR (DMSO-d6, δ): 3.68 (t, 1H), 4.0 (t, 1H), 4.27 (t, 1H), 5.23 (s, 1H), 7.1-7.5 (m, 12H), 11.98 (s, 1H), 12.25 (s, 1H).

Aufarbeitung

  1. customThe reaction mixture was evaporated in vacuo to dryness
  2. filtrationthe precipitate was filtered off
  3. washwashed with ethanol
  4. customdried
  5. customto give 0.39 g of the crude product, which
  6. customwas recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-86446b81494e404a84c039341f23ae1b
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468748

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