Ethylenediamine → N-(2-chloro-4-nitrophenyl)ethane-1,2-diamine

HRID 436338Notes

Reaction equation

[CH2:1]([NH2:4])[CH2:2][NH2:3].[Cl:5][C:6]1[CH:7]=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10][C:11]=1Cl>>[N+:13]([C:8]1[CH:9]=[CH:10][C:11]([NH:3][CH2:2][CH2:1][NH2:4])=[C:6]([Cl:5])[CH:7]=1)([O-:15])=[O:14]

Participants

Reactant 2

HCID 3301Ethylenediamine

HCID 74431,2-Dichloro-4-nitrobenzene

Product 1

HCID 2829584N-(2-chloro-4-nitrophenyl)ethane-1,2-diamine

Procedure

Ethylene diamine is reacted with 3,4-dichloronitrobenzene to form 4-nitro-2-chloro-N-(β-aminoethyl) aniline, which is reacted in an acetic solution with potassium isocyanate to form 4-nitro-2-chloro-N-(β-ureidoethyl) aniline. This latter compound is reduced with hydrazine in the presence of Raney's nickel, yielding 4-amino-2-chloro-N-(β-ureidoethyl) aniline.

Sources & evidence

ORD record: ord-83b9628b4da54dcbb44379db08fb5aa8
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04008272

Reaction notes

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