Aniline → Phenylurea

HRID 1696573Notes

Reaction equation

HRID 1696573 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+]>C(O)(=O)C.O>[C:2]1([NH:1][C:9]([NH2:10])=[O:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 11378442Potassium cyanate

Product 1

HCID 6145PhenylureaYield 50.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of aniline (2.51 g, 27 mmol) dissolved in glacial acetic acid (14 mL) and water (28 mL) was slowly added a solution of potassium cyanate (4.4 g, 54 mmol) dissolved in water (35 mL). The mixture stirred for 2 h at RT, filtered, washed with water and dried under reduced pressure to yield phenylurea as a white solid (1.85 g, 50% yield). 1H NMR (DMSO-d6): δ 8.47 (s, 1H), 7.38 (dd, J=8.4 Hz, 0.9 Hz, 2H), 7.2 (t, J=7.6 Hz, 2H), 6.88 (t, J=7.6 Hz, 1H), 5.81 (brs, 2H); MS (ESI) m/z: 137 (M+H+).

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-b9933de4e34f46adbeac8a84c93e9f2e
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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