Water → N,N′-1,2-Ethanediylbis[4-methyl-N-[3-[[(4-methylphenyl)sulfonyl]amino]propyl]benzenesulfonamide]

HRID 976182Notes

Reaction equation

HRID 976182 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][NH:19][CH2:20][CH2:21][CH2:22][NH2:23].[OH2:24]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:23][CH2:22][CH2:21][CH2:20][N:19]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:18][CH2:17][N:16]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:15][CH2:14][CH2:13][NH:12][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:8])=[O:24])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 25378N,N'-Bis(3-aminopropyl)ethylenediamine

Product 1

HCID 3090848N,N′-1,2-Ethanediylbis[4-methyl-N-[3-[[(4-methylphenyl)sulfonyl]amino]propyl]benzenesulfonamide]Yield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a stirred solution of p-toluenesulfonyl chloride (460 g, 2.41 mole) in pyridine (1.5 l) at 0° C. was added a solution of 1,5,8,12-tetraazadodecane (100 g, 0.574 mole) in pyridine (100 ml) under a dry argon atmosphere, maintaining the temperature ≤50° C. The addition required 1 h. The mixture was allowed to cool to room temperature and was stirred for 2 h. H2O (3 l) was slowly added to the cooled (ice bath) mixture. The resulting brown solid was filtered and washed thoroughly with H2O. The crude product was purified by recrystallization from DMF-H2O to give 238 g (53% yield) of the product as a crude granular solid: mp 141°-2° C.; 1H NMR (CDCl3) δ1.78 (quint, J=6.2 Hz, 4 H), 2.41 (s, 6 H), 2.43 (s, 6 H), 2.97 (quart, J=6.6 Hz, 4 H), 3.15 (t, J=6.6 Hz, 4 H), 3.22 (s, 4 H), 5.31 (t, J=6.5 Hz, 2 H), 7.28 (d, J=8.3 Hz, 4 H), 7.32 (d, J=8.3 Hz, 4 H), 7.66 (d, J=8.3 Hz, 4 H), 7.72 (d, J=8.3 Hz, 4 H).

Workup

  1. temperaturemaintaining the temperature ≤50° C
  2. additionThe addition required 1 h
  3. temperaturecooled (ice bath) mixture
  4. filtrationThe resulting brown solid was filtered
  5. washwashed thoroughly with H2O
  6. customThe crude product was purified by recrystallization from DMF-H2O

Sources & evidence

ORD record
ord-7a704a149c3c4085ba874a10af8333f3
Source dataset
uspto-grants-1997_03
Patent number
US05610293

Reaction notes

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