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

HRID 2287799Notes

Reaction equation

HRID 2287799 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,6 H), 2.41 (s, 6 H), 2.84 (quart, J=6.6 Hz, 4 H), 3.07 (t, J=7.0 Hz, 4 H), 3.12 (s, 4 H), 7.40 (m, 8 H), 7.66 (m, 8 H).

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-10da2be862d04be4a01a291b52025fe4
Source dataset
uspto-grants-2000_07
Patent number
US06084093

Reaction notes

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