Diethyl Ether → 6-Nitro-9-(thiophene-2-sulfonyl)-1,4,7,8,9,10-hexahydro-pyrido[3,4-f]quinoxaline-2,3-dione

HRID 1739676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739676
[N+:1]([C:4]1[C:13]2[N:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]2[C:6](=[N:7][C:8](=[O:19])[C:9](=[O:18])[N:10]=2)[CH:5]=1)([O-:3])=[O:2].Cl[S:21]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)(=[O:23])=[O:22].C(N(CC)CC)C.C(OCC)C>C1COCC1.CN(C=O)C>[N+:1]([C:4]1[C:17]2[CH2:16][CH2:15][N:14]([S:21]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)(=[O:23])=[O:22])[CH2:13][C:12]=2[C:11]2[NH:10][C:9](=[O:18])[C:8](=[O:19])[NH:7][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 727442526-Nitropyridoquinoxalinedione

Produkt 1

HCID 218369506-Nitro-9-(thiophene-2-sulfonyl)-1,4,7,8,9,10-hexahydro-pyrido[3,4-f]quinoxaline-2,3-dioneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of the 6-nitropyridoquinoxalinedione (0.1 g, 0.38 mmol), 2-chlorosulfonyl thiophene (104 mg, 0.57 mmol), triethylamine (70 μl) in THF (5 mL) and DMF (5 mL) was stirred at 60° C. for 24 hours. The mixture was poured onto water and diethyl ether. The precipitate was collected by filtration, washed with water and ether, and dried in vacuo to give product as a yellow solid (80 mg) in 52% yield; mp >300° C. m/e, M+1 409 nmR, IR, CHN.

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water and ether
  3. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f8d22c6dac5d41ce86ba8e324e8b06f6
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05968928

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