Water → 4-methyl-N-[2-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonylamino]ethyl]amino]ethyl]amino]ethyl]benzenesulfonamide

HRID 1683223Notes

Reaction equation

HRID 1683223 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][NH:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][NH2:21].[OH2:22]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:12][CH2:13][CH2:14][N:15]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:16][CH2:17][N:18]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:19][CH2:20][NH:21][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:8])=[O:22])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5565TriethylenetetramineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 3166814-methyl-N-[2-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonylamino]ethyl]amino]ethyl]amino]ethyl]benzenesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a stirred solution of p-toluenesulfonyl chloride (285 g, 1.50 mole) in pyridine (650 ml) at 5° C. was added a solution of 1,4,7,10-tetraazadecane (48.0 g, 0.328 mole) in pyridine (200 ml) under a dry argon atmosphere maintaining the temperature <20° C. The mixture was stirred for 3 days at room temperature. H2O (1 l) was slowly added to the cooled (ice bath) mixture. The solid was filtered, washed thoroughly with H2O and dried in vacuo to give 225 g (90% yield) of the product as a powder: mp 222°-4° C.; 1H NMR (DMSO-d6) δ 2.38 (s, 6H), 2.41 (s, 6H), 2.84 (quart, J=6.6 Hz, 4H), 3.07 (t, J=7.0 Hz, 4H), 3.12 (s, 4H), 7.40 (m, 8H), 7.66 (m, 8H).

Workup

  1. temperaturemaintaining the temperature <20° C
  2. temperaturecooled (ice bath) mixture
  3. filtrationThe solid was filtered
  4. washwashed thoroughly with H2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-4472eaac940e42ed819ef0af1d588fe5
Source dataset
uspto-grants-1997_06
Patent number
US05637578

Reaction notes

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