Urea → 1,3-Bis(4-Aminophenyl)urea

HRID 258800Notes

Reaction equation

HRID 258800 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].[CH:5]1[C:10]([NH2:11])=[CH:9][CH:8]=[C:7](N)[CH:6]=1>O>[CH:9]1[C:10]([NH2:11])=[CH:5][CH:6]=[C:7]([NH:1][C:2]([NH:4][C:7]2[CH:8]=[CH:9][C:10]([NH2:11])=[CH:5][CH:6]=2)=[O:3])[CH:8]=1

Participants

4

Reactant 2

HCID 1176Urea2×HCID 7814P-Phenylenediamine

Product 1

HCID 2257031,3-Bis(4-Aminophenyl)urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 1-liter, 3-neck round-bottom flask equipped with a mechanical stirrer, nitrogen inlet tube extending below the liquid level and a reflux condenser with a nitrogen exit to a gas bubbler, was added 500 ml. of distilled water. After the water was de-oxygenated by bubbling nitrogen gas through it for three hours, 15 g. (0.25 mole) of a commercial pre-dried urea and 60 g. (0.554 mole) of purified p-phenylenediamine were added and the solution which formed was refluxed for about 72 hours under a nitrogen atmosphere. The diamine to urea mole ratio utilized was 2.22.

Workup

  1. customTo a 1-liter, 3-neck round-bottom flask equipped with a mechanical stirrer, nitrogen inlet tube
  2. additionwas added 500 ml
  3. customby bubbling nitrogen gas through it for three hours
  4. customthe solution which formed
  5. temperaturewas refluxed for about 72 hours under a nitrogen atmosphere

Sources & evidence

ORD record
ord-e3d6d1ef0b0c41dc8d912d60346c0030
Source dataset
uspto-grants-1977_07
Patent number
US04035344

Reaction notes

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