Potassium Carbonate → HCID 10013630, compound

HRID 1613358Notes

Reaction equation

HRID 1613358 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][CH2:16][OH:17].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][CH2:16][OH:17])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 823151-(p-Hydroxyphenyl)imidazole

Product 1

HCID 10013630HCID 10013630, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred mixture of 4(1H-imidazol-1-yl)phenol (16.0 g, 0.10 mole), 3-chloropropanol (19.0 g, 0.20 mole), potassium carbonate (28 g, 0.20 mole) and methyl ethyl ketone (100 ml) was heated at reflux temperature for 24 hr. The reaction mixture was cooled, filtered, and the filtrate concentrated. The residue was partitioned between ethyl acetate and 0.01N sodium hydroxide solution. The ethyl acetate layer was dried (magnesium sulfate), diluted with ether, and the solid precipitate collected. The solid was recrystallized from methyl isobutyl ketone to obtain 10.0 g (46%), mp 76°-78° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 24 hr
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customThe residue was partitioned between ethyl acetate and 0.01N sodium hydroxide solution
  7. dry with materialThe ethyl acetate layer was dried (magnesium sulfate)
  8. additiondiluted with ether
  9. customthe solid precipitate collected
  10. customThe solid was recrystallized from methyl isobutyl ketone
  11. customto obtain 10.0 g (46%), mp 76°-78° C.

Sources & evidence

ORD record
ord-91bc5c17ecb1428794891a3acda5f807
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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