2-Aminophenol → (2-Hydroxyphenyl)urea

HRID 965900Notes

Reaction equation

HRID 965900 reaction equation
[O-:1][C:2]#[N:3].[K+].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12]>O.C(O)(=O)C>[OH:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[NH:5][C:2]([NH2:3])=[O:1]

Participants

5

Reactant 2

HCID 58012-AminophenolHCID 11378442Potassium cyanate

Product 1

HCID 70964(2-Hydroxyphenyl)ureaYield 47.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of potassium cyanate (3.94 g, 48.6 mmol) in water (30 mL) was added during 15 min. to suspension of 2-aminophenol (2.41 g, 22.1 mmol) in 50% aqueous acetic acid (160 mL). The resulting solution was allowed to stand at room temperature overnight and then extracted with ethyl ether (3 times). The combined organic extracts was concentrated to small volume and poured into cold saturated aqueous sodium hydrogen carbonate. The solid was filtered and washed with water to afford the subtitle compound (1.61 g, 47.9%).

Workup

  1. extractionextracted with ethyl ether (3 times)
  2. concentrationThe combined organic extracts was concentrated to small volume
  3. additionpoured into cold saturated aqueous sodium hydrogen carbonate
  4. filtrationThe solid was filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-8c5054308d7f42de889fdf222bc89d56
Source dataset
uspto-grants-2005_10
Patent number
US06951874B2

Reaction notes

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