Urea → 1,3-Bis(4-Aminophenyl)urea

HRID 1657352Notes

Reaction equation

HRID 1657352 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 3 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 3 hours
  4. customthe solution which formed
  5. temperaturewas refluxed for about 72 hours under a nitrogen atmosphere

Sources & evidence

ORD record
ord-96b6f87319f74bb7b76fe2118730209d
Source dataset
uspto-grants-1976_06
Patent number
US03960818

Reaction notes

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