2-Amino-4-chlorophenol → (5-Chloro-2-hydroxy-phenyl)-urea

HRID 270136Notes

Reaction equation

HRID 270136 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C([O-])(=O)C.[NH4+].[O-:15][C:16]#[N:17].[K+]>Cl.O>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([OH:9])=[C:2]([NH:1][C:16]([NH2:17])=[O:15])[CH:7]=1

Participants

6

Reactant 3

HCID 72652-Amino-4-chlorophenolHCID 517165Ammonium AcetateHCID 11378442Potassium cyanate

Product 1

HCID 11435385(5-Chloro-2-hydroxy-phenyl)-urea

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

2-amino-4-chlorophenol (1.3 g, 8.9 mmol) was dissolved in 1M HCl (10 mL). Ammonium acetate was added to the solution to adjust pH to 5. The stirred mixture was treated with a suspension of potassium cyanate (0.80 mg, 9.8 mmol) in water, and than kept overnight at room temperature. Water was removed by evaporation and the residue was recrystallized from water to afford pink precipate (0.9 g, 55%).

Workup

  1. customWater was removed by evaporation
  2. customthe residue was recrystallized from water
  3. customto afford pink precipate (0.9 g, 55%)

Sources & evidence

ORD record
ord-9e7739100d6f46b6835f31dc24899cd2
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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