Ethylenediamine → 4-nitro-2-methyl-N-(beta-ureido-ethyl)aniline

HRID 436332

Reaction equation

C(N)CN.ClC1C=CC([N+]([O-])=O)=CC=1C.Cl.[N+:17]([C:20]1[CH:29]=[CH:28][C:23]([NH:24][CH2:25][CH2:26][NH2:27])=[C:22]([CH3:30])[CH:21]=1)([O-:19])=[O:18].[N-:31]=[C:32]=[O:33].[K+]>>[N+:17]([C:20]1[CH:29]=[CH:28][C:23]([NH:24][CH2:25][CH2:26][NH:27][C:32]([NH2:31])=[O:33])=[C:22]([CH3:30])[CH:21]=1)([O-:19])=[O:18]

Participants

Reactant 4

HCID 3301Ethylenediamine

HCID 83315Benzene, 1-chloro-2-methyl-4-nitro-

HCID 11051572Potassio isocyanate

HCID 17336835N-(2-methyl-4-nitrophenyl)ethane-1,2-diamine hydrochloride

Product 1

HCID 214541964-nitro-2-methyl-N-(beta-ureido-ethyl)aniline

Procedure

4-nitro-2-methyl-N-(β-aminoethyl) aniline monohydrochloride is obtained by reacting ethylene diamine with 2-chloro-5-nitro-toluene. This monohydrochloride is then reacted with potassium isocyanate to produce 4-nitro-2-methyl-N-(β-ureidoethyl) aniline, which is reduced with hydrazine and Raney's nickel to 4-amino-2-methyl-N-(β-ureidoethyl) aniline.

Sources & evidence

ORD record: ord-d9cb57c3fa2f41339e62a27c145c8718
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04008272

Linked notes

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