Ethylenediamine → 2-{2-[(2-Aminoethyl)amino]-5-nitrobenzene-1-sulfonyl}ethan-1-ol

HRID 981809Notes

Reaction equation

HRID 981809 reaction equation
[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1Cl)(=[O:6])=[O:5].[NH2:17][CH2:18][CH2:19][NH2:20]>>[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[NH:17][CH2:18][CH2:19][NH2:20])(=[O:6])=[O:5]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 136286432-Chloro-5-nitrophenyl hydroxyethyl sulfone2×

Product 1

HCID 136286482-{2-[(2-Aminoethyl)amino]-5-nitrobenzene-1-sulfonyl}ethan-1-olYield 94.5%

Procedure

132.85 g of 2-chloro-5-nitrophenyl hydroxyethyl sulfone are added at 65°-70° C. with stirring to 250 g of 1,2-diaminoethane in the course of 15 minutes, and the mixture is stirred at this temperature for a further 15 minutes. The reaction mixture is then allowed to cool down to room temperature with stirring and is poured onto 1 l of ice-water, and the product is isolated by filtration. This gives 139.6 g (2-β-aminoethylamino)-5-nitrophenyl hydroxyethyl sulfone having a melting point of 147° C. and a purity of >98%, which corresponds to a yield of 94.5% of theory, relative to starting 2-chloro-5-nitrophenyl hydroxyethyl sulfone.

Workup

  1. stirringwith stirring
  2. customthe product is isolated by filtration

Sources & evidence

ORD record
ord-ba01374305104baead49f7ee7cda0739
Source dataset
uspto-grants-1991_02
Patent number
US04992589

Reaction notes

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