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

HRID 1683216Notes

Reaction equation

HRID 1683216 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

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, 4H), 2.42 (s, 6H), 2.43 (s, 3H), 2.96 (quart, J=6.4 Hz, 4H), 3.11 (t, J=6.8 Hz, 4H), 5.12 (t, J=6.6 Hz, 2H), 7.30 (m, 6H), 7.63 (m, 2H), 7.73 (m, 4H).

Workup

  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. dry with materialdried (MgSO4)
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0f7d522247134c62a39e281e6b3f0436
Source dataset
uspto-grants-1997_06
Patent number
US05637578

Reaction notes

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