Ethylenediamine → p-Toluenesulfonamide, N,N'-ethylenebis-

HRID 263277Notes

Reaction equation

HRID 263277 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1.[OH-:16].[Na+]>CCOCC>[S:11]([NH:3][CH2:2][CH2:1][NH:4][S:11]([C:8]1[CH:9]=[CH:10][C:5]([CH3:15])=[CH:6][CH:7]=1)(=[O:12])=[O:16])([C:8]1[CH:9]=[CH:10][C:5]([CH3:15])=[CH:6][CH:7]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 95237p-Toluenesulfonamide, N,N'-ethylenebis-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Treat ethylenediamine with p-toluenesulfonyl chloride (i.e. tosyl chloride) and sodium hydroxide in aqueous ether according to known procedures to obtain N,N'-ditosylethylenediamine.

Sources & evidence

ORD record
ord-dda94c5143d2401197c1116a206ee9d3
Source dataset
uspto-grants-1979_05
Patent number
US04156683

Reaction notes

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