2-Aminophenol → (2-Hydroxyphenyl)urea

HRID 584618Notes

Reaction equation

HRID 584618 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-c7aedfa9d4cb463fa739f736eb003698
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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