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p-Toluenesulfonic acid → 1-Cyclohexyl-6-(3-formyl-1-pyrrolyl)-7-nitro-2,3(1H,4H)-quinoxalinedione

HRID 861533
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 861533
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:19])[C:8](=[O:18])[N:9]2C2CCCCC2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].[CH:23]([CH:25]1[CH2:29][CH:28](OC)O[CH:26]1OC)=[O:24].[C:34]1(C)[CH:39]=[CH:38][C:37](S(O)(=O)=O)=[CH:36][CH:35]=1>CN(C)C=O.C1(C)C=CC=CC=1>[CH:34]1([N:6]2[C:5]3[C:10](=[CH:11][C:2]([N:1]4[CH:28]=[CH:29][C:25]([CH:23]=[O:24])=[CH:26]4)=[C:3]([N+:20]([O-:22])=[O:21])[CH:4]=3)[NH:9][C:8](=[O:18])[C:7]2=[O:19])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1
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Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehydeHCID 220970767-Amino-1-cyclohexyl-6-nitro-2,3(1H,4H)-quinoxalinedione

Produkt 1

HCID 220972041-Cyclohexyl-6-(3-formyl-1-pyrrolyl)-7-nitro-2,3(1H,4H)-quinoxalinedioneAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21735183
Dimethylformamide toluene
Lösungsmittel

Versuchsvorschrift

4 g (13 mmol) of the product 37b, 2.3 g (14 mmol) of 3-formyl-2,5-dimethoxytetrahydrofuran and a spatula tip of 4-toluenesulfonic acid in 200 ml of dimethylformamide/toluene (1:1) were refluxed with a water trap. After the reaction was complete (TLC check), the mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated under reduced pressure. This residue was purified by chromatography on silica gel (mobile phase: toluene/acetone/glacial acetic acid=40/20/1) to yield 1.1 g (22%) of the product.

Aufarbeitung

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure
  5. customThis residue was purified by chromatography on silica gel (mobile phase: toluene/acetone/glacial acetic acid=40/20/1)

Quellen und Nachweise

ORD-Eintrag
ord-f46f7893d50f46868cd06b6fe822a852
Quelldatensatz
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05714489

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