Ethylenediamine → 4-nitro-2-methoxy-N-(beta-aminoethyl)aniline

HRID 436335Notes

Reaction equation

HRID 436335 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].Cl[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[O:15][CH3:16]>>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([NH:3][CH2:2][CH2:1][NH2:4])=[C:7]([O:15][CH3:16])[CH:8]=1)([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 705192-Chloro-5-nitroanisole

Product 1

HCID 214541994-nitro-2-methoxy-N-(beta-aminoethyl)aniline

Procedure

Ethylene diamine is reacted with 2-chloro-5-nitroanisole to form 4-nitro-2-methoxy-N-(β-aminoethyl)aniline which is isolated in the form of its monohydrochloride. This monohydrochloride is reacted with potassium isocyanate to form 4-nitro-2-methoxy-N-(β-ureidoethyl) aniline which is reduced by a sodium hydrosulfite solution to 4-amino-2-methoxy-N-(β-ureidoethyl) aniline.

Sources & evidence

ORD record
ord-4407622358fd42e5abcb1749bf0a6cdf
Source dataset
uspto-grants-1977_02
Patent number
US04008272

Reaction notes

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