N,N-Dimethylethylenediamine → HCID 10244493, Verbindung

HRID 1160628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160628
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].Cl[C:8]1[N:9]=[N+:10]([O-:20])[C:11]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:12]=2[N:13]=1>COCCOC>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:11]2[N+:10]([O-:20])=[N:9][C:8]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[N:13][C:12]=2[CH:14]=1

Komponenten

4

Edukt 2

HCID 66053N,N-DimethylethylenediamineHCID 16081296HCID 16081296, Verbindung

Produkt 1

HCID 10244493HCID 10244493, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

N,N-Dimethyl-1,2-ethanediamine (1.33 mL, 12.1 mmol) was added to a stirred solution of chloride 7 (0.85 g, 4.04 mmol) in DME (50 mL) and the solution stirred at reflux temperature for 16 h. The solvent was evaporated and the residue was partitioned between DCM (100 mL) and dilute aqueous NH3 (50 mL). The organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-5%) of MeOH/DCM, to give amine 8 (0.72 g, 68%) which was dissolved in HCl-saturated MeOH, the solvent evaporated and the residue crystallized as a tan solid, mp (MeOH/EtOAc) 236-239° C.; 1H NMR [(CD3)2SO] δ 10.68 (br s, 1 H, NH+Cl−), 8.07 (d, J=9.3 Hz, 1 H, H-8), 8.03 (br s, 1 H, NH), 6.95-6.99 (m, 2 H, H-5, H-7), 3.92 (s, 3 H, OCH3), 3.70-3.76 (m, 2 H, CH2N), 3.30-3.35 (m, 2 H, CH2N), 2.81 [d, J=4.9 Hz, 6 H, N(CH3)2]; 13C NMR [(CD3)2SO] δ 164.9, 159.0, 150.4, 125.4, 121.6, 117.3, 104.3, 55.2, 55.0, 42.3 (2), 35.8. Anal. Calcd for C12H18ClN5O2: C, 48.1; H, 6.1; N, 23.4; Cl, 11.8. Found: C, 48.3; H, 6.1; N, 23.6; Cl, 11.9%.

Aufarbeitung

  1. temperatureat reflux temperature for 16 h
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between DCM (100 mL) and dilute aqueous NH3 (50 mL)
  4. customThe organic fraction was dried
  5. customthe solvent evaporated
  6. customThe residue was purified by chromatography
  7. washeluting with a gradient (0-5%) of MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-e56f2bcb6d234b83b5bbfa2e0d8d4c5e
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816521B2

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