2-Chloroethanol → 2-[4-(1H-imidazol-1-yl)phenoxy]ethanol

HRID 1613437Notes

Reaction equation

HRID 1613437 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl[CH2:14][CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:14][CH2:15][OH:16])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 823151-(p-Hydroxyphenyl)imidazole

Product 1

HCID 100816222-[4-(1H-imidazol-1-yl)phenoxy]ethanolYield 50%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred mixture of 8.0 g (0.050 mole) of 4(1H-imidazol-1-yl)phenol, 13.5 ml (0.20 mole) of 2-chloroethanol and 28 g (0.2 mole) of potassium carbonate in 200 ml of methyl ethyl ketone was heated at reflux, filtered, and concentrated to obtain 5.1 g of 2-[4-(1H-imidazol-1-yl)phenoxy]ethanol (50%). This alcohol (0.25 mole) and 5.2 g (0.030 mole) of sulfamic acid phenyl ester (Example 33) in 100 ml of dioxane was heated at reflux for 20 minutes, concentrated and the residual solid triturated in acetone. The triturant was acidified with an anhydrous solution of hydrogen chloride in isopropyl alcohol and the solid hydrochloride collected by filtration. The product was recrystallized from isopropyl alcohol-isopropyl ether to yield 4.26 g of solid, monohydrochloride, mp 156°-157° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-306cb22a042941c8b7a4015e8e2a4c60
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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