N,N,N'-Trimethyl-N'-(6-nitro-benzothiazol-2-yl)ethane-1,2-diamine → N2-(2-Dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamine

HRID 1174907

Reaktionsgleichung

Reaktionsgleichung von HRID 1174907
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]([CH3:18])[C:6]1[S:7][C:8]2[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:9]=2[N:10]=1.[H][H]>[Pd].CCO.C1COCC1>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]([CH3:18])[C:6]1[S:7][C:8]2[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:9]=2[N:10]=1

Komponenten

6

Edukt 2

HCID 57771682N,N,N'-Trimethyl-N'-(6-nitro-benzothiazol-2-yl)ethane-1,2-diamineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 55226563N2-(2-Dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Combine N,N,N′-Trimethyl-N′-(6-nitro-benzothiazol-2-yl)ethane-1,2-diamine (5.79 g, 20.6 mmol) and 5% palladium on carbon (5.02 g) in EtOH (200 mL) and THF (25 mL). Shake on a Parr shaker at 60 psi of hydrogen at room temperature for 18 h. Filter the reaction mixture through filter paper, wash with EtOH (50 mL), and concentrate in vacuo to afford the crude title compound (4.1 g, 80%). The crude product was carried on as is. 1H NMR (400 MHz, DMSO-d6): δ 7.10 (d, 1H, J=8.4 Hz), 6.86 (d, 1H, J=1.8 Hz), 6.52 (dd, 1H, J=8.4, 2.2 Hz), 4.80 (br s, 2H), 3.51 (t, 2H, J=6.6 Hz), 3.04 (s, 3H), 2.48 (m, 2H), 2.18 (s, 6H).

Aufarbeitung

  1. filtrationFilter the reaction mixture
  2. filtrationthrough filter paper
  3. washwash with EtOH (50 mL)
  4. concentrationconcentrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9bad5bb8fc5448a8aeec4eb3d64681ad
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838543B2

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