Potassium cyanate → N-[4-[2-(1H-Imidazol-1-yl)ethoxy]phenyl]urea

HRID 745922Notes

Reaction equation

HRID 745922 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:4][CH:3]=1.[O-:16][C:17]#[N:18].[K+]>Cl.O>[NH:1]([C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:14][CH:15]=1)[C:17]([NH2:18])=[O:16]

Participants

5

Reactant 2

HCID 11378442Potassium cyanateHCID 135692034-[2-(1H-Imidazol-1-yl)ethoxy]aniline

Product 1

HCID 13569204N-[4-[2-(1H-Imidazol-1-yl)ethoxy]phenyl]ureaYield 82.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

1-[2-(4-Aminophenoxy)ethyl]imidazole (0.6 g) was dissolved in 1N hydrochloric acid (3.0 ml) and a solution of potassium cyanate (0.3 g) in 1 ml of water was added. The mixture was allowed to stand at room temperature for 15 minutes and the resulting solid was filtered off, washed with water and crystallised from water to give 1-[2-(4-ureidophenoxy)ethyl]imidazole (0.6 g), m.p. 199°-201° C. Found: C, 58.20; H, 5.70; N, 23.06. C12H14N4O2 requires: C, 58.52; H, 5.73; N, 22.75%.

Workup

  1. filtrationthe resulting solid was filtered off
  2. washwashed with water
  3. customcrystallised from water

Sources & evidence

ORD record
ord-acc04cf877aa4dcd9b62f88b27580a76
Source dataset
uspto-grants-1986_07
Patent number
US04602016

Reaction notes

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