Bis(3-aminopropyl)amine → Bis(3-{[(4-methylphenyl)sulfonyl]amino}propyl)[(4-methylphenyl)sulfonyl]amine

HRID 2287792

Reaktionsgleichung

Reaktionsgleichung von HRID 2287792
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][CH2:19][NH2:20]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:12][CH2:13][CH2:14][CH2:15][N:16]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:17][CH2:18][CH2:19][NH:20][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 5942Bis(3-aminopropyl)amineHCID 73974-Toluenesulfonyl chloride

Produkt 1

HCID 373797Bis(3-{[(4-methylphenyl)sulfonyl]amino}propyl)[(4-methylphenyl)sulfonyl]amineAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

To a stirred solution of p-toluenesulfonyl chloride (240 g, 1.26 mole) in pyridine (600 ml) at 0° C. was added a solution of 1,5,9-triazanonane (50.0 g, 0.381 mole) in pyridine (100 ml) under a dry nitrogen atmosphere, maintaining the temperature ≤60° C. The addition required 15 minutes. The solvent was removed in vacuo and the resulting yellow oil was dissolved in ethyl acetate (1 l) and H2O (500 ml). The ethyl acetate layer was separated, washed with 0.1 N HCl, H2O and saturated NaCl solution and dried (MgSo4). The solution was decolorized with silica gel and the solvent was removed in vacuo to give 133 g (59% yield) of the crude product as a glassy solid: 1H NMR (CDCl3) δ 1.71 (quint, J=6.6 Hz, 4 H), 2.42 (s, 6 H), 2.43 (s, 3 H), 2.96 (quart, J=6.4 Hz, 4 H), 3.11 (t, J=6.8 Hz, 4 H), 5.12 (t, J=6.6 Hz, 2 H), 7.30 (m, 6 H), 7.63 (m, 2 H), 7.73 (m, 4 H).

Aufarbeitung

  1. temperaturemaintaining the temperature ≤60° C
  2. additionThe addition required 15 minutes
  3. customThe solvent was removed in vacuo
  4. dissolutionthe resulting yellow oil was dissolved in ethyl acetate (1 l)
  5. customThe ethyl acetate layer was separated
  6. washwashed with 0.1 N HCl, H2O and saturated NaCl solution
  7. customdried (MgSo4)
  8. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dca70a0a5bc2470fbb9e28f59ef11070
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06084093

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