Aniline → Phenylurea

HRID 470155Notes

Reaction equation

HRID 470155 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:8][C:9]#[N:10].[K+]>Cl>[C:2]1([NH:1][C:9]([NH2:10])=[O:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 11378442Potassium cyanate

Product 1

HCID 6145PhenylureaYield 94%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
2 °C

Procedure

Aniline (18.6 g, 200 mmol) was dissolved in 100 ml of 2M hydrochloric acid (aq.), cooled down to 2° C. by immersing in ice bath, charged with potassium cyanate (19.5 g, 240 mmol) portion wise in 30 minutes under stirring, the cooling was removed and stirred for 4 h at room temperature, whereby thick white solids precipitated. The reaction mixture was stored at 4° C. for 1 h. The solids were separated by filtration, washed well with ice cold water and dried under vacuum yielding pure white solids (25.6 g, 94%).

Workup

  1. customthe cooling was removed
  2. stirringstirred for 4 h at room temperature
  3. customwhereby thick white solids precipitated
  4. customThe solids were separated by filtration
  5. washwashed well with ice cold water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c4baa714c8154f9a9356a73eb451dec3
Source dataset
uspto-grants-2014_01
Patent number
US08629272B2

Reaction notes

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