Acetic Acid → 1-(2-Ureidoethylamino)-4-nitrobenzene

HRID 436330Notes

Reaction equation

HRID 436330 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.C(O)(=O)C.[N-:18]=[C:19]=[O:20].[K+]>O>[NH:1]([CH2:2][CH2:3][NH:4][C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[C:19]([NH2:18])=[O:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 236318N-(2-aminoethyl)-N-(4-nitrophenyl)amineHCID 11051572Potassio isocyanate

Product 1

HCID 73423441-(2-Ureidoethylamino)-4-nitrobenzeneYield 73.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

37 g (0.2 mole) of para-[N-(β-amino-ethyl)]amino nitrobenzene is dissolved in 200 cm3 of water at 30° C, to which 15 cm3 (0.26 mole) of acetic acid had been added. 17 g (0.21 mole) of potassium isocyanate is then rapidly added. The desired product precipitates immediately in a form which is very difficult to dry. 150 cm3 of acetic acid is added to the reaction mixture and it is heated until the urein is completely dissolved. After slow cooling, drying yields 33 g of para-[N-(β-ureidoethyl)]amino nitrobenzene in a well crystallized form, which is practically prue and melts at 187° C.

Workup

  1. additionhad been added
  2. customThe desired product precipitates immediately in a form which
  3. customto dry
  4. addition150 cm3 of acetic acid is added to the reaction mixture and it
  5. temperatureis heated until the urein
  6. dissolutionis completely dissolved
  7. customAfter slow cooling, drying

Sources & evidence

ORD record
ord-38e11ac44724494e9dbb52653c6ae6b1
Source dataset
uspto-grants-1977_02
Patent number
US04008272

Reaction notes

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