4-Chloro-3-nitrobenzenesulfonamide → 4-(4-Methylpiperazin-1-ylamino)-3-nitrobenzenesulfonamide

HRID 574767

Reaktionsgleichung

Reaktionsgleichung von HRID 574767
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.Cl.[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([NH2:24])[CH2:20][CH2:19]1.CN(C)CCN(C)C>O1CCOCC1>[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([NH:24][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:20][CH2:19]1

Komponenten

5

Edukt 3

HCID 73244-Chloro-3-nitrobenzenesulfonamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 1982214-Methylpiperazin-1-ylamine dihydrochloride hydrate

Produkt 1

HCID 47377414-(4-Methylpiperazin-1-ylamino)-3-nitrobenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A 50 mL round-bottomed flask was charged with 4-chloro-3-nitrobenzenesulfonamide (1 g, 4.23 mmol), 4-methylpiperazin-1-amine dihydrochloride (1 g, 5.32 mmol), and N1,N1,N2,N2-tetramethylethane-1,2-diamine (3 mL, 20.01 mmol) in dioxane (10 mL). The reaction mixture was refluxed for 12 hours. After this time, the reaction mixture was cooled to room temperature, the salt filtered off via a Buchner funnel, and the solvent removed in vacuo. The crude product was added to a silica gel column (Analogix, SF65-200 g) and purified by eluting with 0-5% methanol in dichloromethane.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. filtrationthe salt filtered off via a Buchner funnel
  3. customthe solvent removed in vacuo
  4. additionThe crude product was added to a silica gel column (Analogix
  5. customSF65-200 g) and purified
  6. washby eluting with 0-5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-254c940763bb446c9c0bf28987f0e297
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034875B2

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