Potassium Carbonate → HCID 10058728, compound

HRID 327639Notes

Reaction equation

HRID 327639 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:20]([OH:22])[CH3:21]>C(C(C)=O)C>[N:1]1([C:6]2[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=2)[O:12][CH2:21][CH2:20][OH:22])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 104645913-(1H-Imidazol-1-yl)phenolHCID 126390351-Chloroethan-1-ol2×

Product 1

HCID 10058728HCID 10058728, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A slurry of 16.0 g (0.10 mole) of 3-(imidazol-1-yl)phenol and 42 g (0.3 mole) of potassium carbonate in 100 ml of methyl ethyl ketone was heated to reflux with stirring. The mixture was treated with 25.5 g (0.3 mole) of chloroethanol by dropwise addition over a 2 hr period. The mixture was heated at reflux for an additional 18 hr then treated with an additional 16.1 g (0.2 mole) of chloroethanol and 27.6 (0.2 mol) of potassium carbonate. After an additional 22 hr heating at reflux all starting material was consumed. The reaction mixture was filtered and the filtrate was concentrated. The residue was partitioned between methylene chloride and 0.1N sodium hydroxide solution. The organic layer was concentrated and the residue was crystallized from ethyl acetate to give 10.2 g (50%) of the title compound as tan crystals, mp 81.0°-83.0° C.

Workup

  1. temperatureto reflux
  2. temperatureThe mixture was heated
  3. temperatureat reflux for an additional 18 hr
  4. temperatureAfter an additional 22 hr heating
  5. temperatureat reflux all starting material
  6. customwas consumed
  7. filtrationThe reaction mixture was filtered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was partitioned between methylene chloride and 0.1N sodium hydroxide solution
  10. concentrationThe organic layer was concentrated
  11. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ea8ebe88293547d6859ad73c595ef876
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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