Acetic Acid → (2-Chloro-5-methoxyphenyl)urea

HRID 1786284Notes

Reaction equation

HRID 1786284 reaction equation
Cl.[Cl:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH2:5].C(O)(=O)C.[O-:16][C:17]#[N:18].[K+]>O>[Cl:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH:5][C:17]([NH2:18])=[O:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 27239002-Chloro-5-methoxyanilinium chlorideHCID 11378442Potassium cyanate

Product 1

HCID 21093757(2-Chloro-5-methoxyphenyl)ureaYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
30 °C

Procedure

2-Chloro-5-methoxyaniline hydrochloride (26 g, 134 mmol) was added to acetic acid (117 ml) and water (13 ml). The slurry was warmed to 30° C. A solution of potassium cyanate (13 g, 161 mmol) in water (104 ml) was added dropwise. After 1 hour at 40° C., the reaction was cooled to 20° C., filtered and washed with water (78 ml). The product was dried overnight in vacuo at 60° C. to yield the title compound as a white solid (21.8 g, 81%).

Workup

  1. temperaturethe reaction was cooled to 20° C.
  2. filtrationfiltered
  3. washwashed with water (78 ml)
  4. customThe product was dried overnight in vacuo at 60° C.

Sources & evidence

ORD record
ord-720b28c5db0f4890a338ebe8e375c616
Source dataset
uspto-grants-2009_03
Patent number
US07507742B2

Reaction notes

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