N-(2-chloro-4-nitrophenyl)ethane-1,2-diamine → 4-nitro-2-chloro-N-(beta-ureidoethyl) aniline

HRID 436340Notes

Reaction equation

HRID 436340 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([NH:8][CH2:9][CH2:10][NH2:11])=[C:6]([Cl:14])[CH:5]=1)([O-:3])=[O:2].[N-:15]=[C:16]=[O:17].[K+]>O.C(O)(=O)C>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([NH:8][CH2:9][CH2:10][NH:11][C:16]([NH2:15])=[O:17])=[C:6]([Cl:14])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 2829584N-(2-chloro-4-nitrophenyl)ethane-1,2-diamineHCID 11051572Potassio isocyanate

Product 1

HCID 537590294-nitro-2-chloro-N-(beta-ureidoethyl) anilineYield 92.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

100 g (0.46 mole) of 4-nitro-2-chloro-N-(β-aminoethyl) aniline is dissolved in a liter of water to which 29 cm3 of acetic acid has been added. 41.3 g (0.51 mole) of potassium isocyanate is added to this reaction mixture, which is then left at the ambient temperature for 2 hours. Drying yields 110 g of 4-nitro-2-chloro-N-(β-ureidoethyl) aniline which, after washing with dilute acetic acid and with water, followed by recrystallization in nitromethane, melts at 188° C.

Workup

  1. additionhas been added
  2. customDrying

Sources & evidence

ORD record
ord-0973337edab04f94980b7c48504e401e
Source dataset
uspto-grants-1977_02
Patent number
US04008272

Reaction notes

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