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

HRID 861489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861489
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[N:8]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:7](=[O:21])[C:6](=[O:22])[NH:5]2.[CH3:23][O:24][C:25]([C:27]1(OC)[CH2:31][CH2:30][CH:29](OC)O1)=[O:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C=O.C1(C)C=CC=CC=1>[CH:15]1([N:8]2[C:9]3[C:4](=[CH:3][C:2]([N:1]4[CH:29]=[CH:30][CH:31]=[C:27]4[C:25]([O:24][CH3:23])=[O:26])=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=3)[NH:5][C:6](=[O:22])[C:7]2=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

6

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 13152840Methyl tetrahydro-2,5-dimethoxyfuroateHCID 220970786-Amino-1-cyclohexyl-7-nitro-2,3(1H,4H)-quinoxalinedione

Produkt 1

HCID 220971601-Cyclohexyl-6-(2-methoxycarbonyl-1-pyrrolyl)-7-nitro-2,3(1H,4H)-quinoxalinedioneAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

10 g (33 mmol) of 6-amino-1-cyclohexyl-7-nitro-2,3(1H,4H)-quinoxalinedione (Example 28e), 6.9 g (36 mmol) of 2-methoxycarbonyl-2,5-dimethoxytetrahydrofuran and a spatula tip of p-toluenesulfonic acid were refluxed in a mixture of 50 ml of dimethylformamide and 50 ml of toluene with a water trap. After reaction was complete, the mixture was concentrated under reduced pressure, and the residue was treated with water. The precipitate was filtered off with suction to yield 11 g (79%) of the product. Melting point 211°-212° C.

Aufarbeitung

  1. customAfter reaction
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionthe residue was treated with water
  4. filtrationThe precipitate was filtered off with suction

Quellen und Nachweise

ORD-Eintrag
ord-a76a64408e5b4558ac97d49e6a2cf814
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05714489

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