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 1174907Notes

Reaction equation

HRID 1174907 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-9bad5bb8fc5448a8aeec4eb3d64681ad
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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