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

HRID 976180

Reaktionsgleichung

Reaktionsgleichung von HRID 976180
[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 0.1N 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) δ1.71 (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 0.1N HCl, H2O and saturated NaCl solution
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8a1496379aea4c7c9c64f669c0b49a23
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05610293

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