4-Toluenesulfonyl chloride → N,N'-{[(4-Methylbenzene-1-sulfonyl)azanediyl]di(ethane-2,1-diyl)}bis(4-methylbenzene-1-sulfonamide)

HRID 980783Notes

Reaction equation

HRID 980783 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][NH2:18].[OH-:19].[Na+]>CCOCC.O>[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][NH:18][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:8])=[O:19])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8111DiethylenetriamineHCID 14798Sodium Hydroxide

Product 1

HCID 316685N,N'-{[(4-Methylbenzene-1-sulfonyl)azanediyl]di(ethane-2,1-diyl)}bis(4-methylbenzene-1-sulfonamide)Yield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of p-toluenesulfonyl chloride (191 g) in ether (500 ml) was added drop by drop to a solution of diethylene triamine (38 ml) and sodium hydroxide (40 g) in water (250 ml). The mixture was stirred for one hour at room temperature. A white precipitate was formed and was collected by filtration, washed with water, and then recrystalized using methanol. (Acetonitrile could also be used). The melting point of the recrystalized precipitate was 174° to 175° C. The yield was 90%, and should always be above 70%.

Workup

  1. customA white precipitate was formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customrecrystalized
  5. customwas 174° to 175° C

Sources & evidence

ORD record
ord-e2bc0d0c6e114e16a9faae769a0193b1
Source dataset
uspto-grants-1987_01
Patent number
US04639365

Reaction notes

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